N-methyl-2-indolinone; tetrapropylammonium perruthennate in dichloromethane

1.1: 83 percent / TFA 2.1: H2O2 / Na2WO4 2.2: 25 percent / NaHCO3 3.1: 60 percent / Et2NH 4.1: 63 percent / EDC; HOBt; N-ethylmorpholine 5.1: LiOH 6.1: 61 percent / EDC; HOBt; N-ethylmorpholine 7.1: LiOH 8.1: aq. HCl / acetic acid 9.1: pentafluorophenyl diphenylphosphinate; N-ethylmorpholine / dimethylformamide 10.1: TBAF; MS 4A / tetrahydrofuran / 24 h 11.1: 88 percent / TPAP; NMO; MS 4A / CH2Cl2 View Scheme

1: 68 percent / NaH 2: 70 percent / PCC 3: 100 percent 4: 89 percent 5: 79 percent / TBAF 6: 59 percent / PPh3; CBr4 7: 35 percent / Mg; CuBr*SMe2 8: 63 percent / EDC; HOBt; N-ethylmorpholine 9: LiOH 10: 61 percent / EDC; HOBt; N-ethylmorpholine 11: LiOH 12: aq. HCl / acetic acid 13: pentafluorophenyl diphenylphosphinate; N-ethylmorpholine / dimethylformamide 14: TBAF; MS 4A / tetrahydrofuran / 24 h 15: 88 percent / TPAP; NMO; MS 4A / CH2Cl2 View Scheme

1: 91 percent / EDC; HOBt; N-ethylmorpholine 2: 66 percent / aq. HCl / ethyl acetate 3: 61 percent / EDC; HOBt; N-ethylmorpholine 4: LiOH 5: aq. HCl / acetic acid 6: pentafluorophenyl diphenylphosphinate; N-ethylmorpholine / dimethylformamide 7: TBAF; MS 4A / tetrahydrofuran / 24 h 8: 88 percent / TPAP; NMO; MS 4A / CH2Cl2 View Scheme

1: 70 percent / PCC 2: 100 percent 3: 89 percent 4: 79 percent / TBAF 5: 59 percent / PPh3; CBr4 6: 35 percent / Mg; CuBr*SMe2 7: 63 percent / EDC; HOBt; N-ethylmorpholine 8: LiOH 9: 61 percent / EDC; HOBt; N-ethylmorpholine 10: LiOH 11: aq. HCl / acetic acid 12: pentafluorophenyl diphenylphosphinate; N-ethylmorpholine / dimethylformamide 13: TBAF; MS 4A / tetrahydrofuran / 24 h 14: 88 percent / TPAP; NMO; MS 4A / CH2Cl2 View Scheme

1: 100 percent 2: 89 percent 3: 79 percent / TBAF 4: 59 percent / PPh3; CBr4 5: 35 percent / Mg; CuBr*SMe2 6: 63 percent / EDC; HOBt; N-ethylmorpholine 7: LiOH 8: 61 percent / EDC; HOBt; N-ethylmorpholine 9: LiOH 10: aq. HCl / acetic acid 11: pentafluorophenyl diphenylphosphinate; N-ethylmorpholine / dimethylformamide 12: TBAF; MS 4A / tetrahydrofuran / 24 h 13: 88 percent / TPAP; NMO; MS 4A / CH2Cl2 View Scheme

1: 91 percent / EDC; HOBt; N-ethylmorpholine 2: 66 percent / aq. HCl / ethyl acetate 3: 61 percent / EDC; HOBt; N-ethylmorpholine 4: LiOH 5: aq. HCl / acetic acid 6: pentafluorophenyl diphenylphosphinate; N-ethylmorpholine / dimethylformamide 7: TBAF; MS 4A / tetrahydrofuran / 24 h 8: 88 percent / TPAP; NMO; MS 4A / CH2Cl2 View Scheme

1: 63 percent / EDC; HOBt; N-ethylmorpholine 2: LiOH 3: 61 percent / EDC; HOBt; N-ethylmorpholine 4: LiOH 5: aq. HCl / acetic acid 6: pentafluorophenyl diphenylphosphinate; N-ethylmorpholine / dimethylformamide 7: TBAF; MS 4A / tetrahydrofuran / 24 h 8: 88 percent / TPAP; NMO; MS 4A / CH2Cl2 View Scheme

1: 35 percent / Mg; CuBr*SMe2 2: 63 percent / EDC; HOBt; N-ethylmorpholine 3: LiOH 4: 61 percent / EDC; HOBt; N-ethylmorpholine 5: LiOH 6: aq. HCl / acetic acid 7: pentafluorophenyl diphenylphosphinate; N-ethylmorpholine / dimethylformamide 8: TBAF; MS 4A / tetrahydrofuran / 24 h 9: 88 percent / TPAP; NMO; MS 4A / CH2Cl2 View Scheme

1: 63 percent / EDC; HOBt; N-ethylmorpholine 2: LiOH 3: 61 percent / EDC; HOBt; N-ethylmorpholine 4: LiOH 5: aq. HCl / acetic acid 6: pentafluorophenyl diphenylphosphinate; N-ethylmorpholine / dimethylformamide 7: TBAF; MS 4A / tetrahydrofuran / 24 h 8: 88 percent / TPAP; NMO; MS 4A / CH2Cl2 View Scheme