Dibutyltin dichloride → 3-[(4-Morpholin-4-yl-phenylamino)-methyl]1H-indole-6-carboxylic acid methyl ester

HRID 416242

반응식

HRID 416242 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH:14]=O)=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].[O:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH2:14][NH:26][C:25]3[CH:24]=[CH:23][C:22]([N:19]4[CH2:20][CH2:21][O:16][CH2:17][CH2:18]4)=[CH:28][CH:27]=3)=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4]

참가 물질

6

반응물 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 735867methyl 3-formyl-1H-indole-6-carboxylate

생성물 1

HCID 589306603-[(4-Morpholin-4-yl-phenylamino)-methyl]1H-indole-6-carboxylic acid methyl ester수율 98%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-formyl-1H-indole-6-carboxylic acid methyl ester (500 mg, 2.46 mmol), 4-morpholinoaniline (482.3 mg, 2.71 mmol) and dibutyltin dichloride (76 mg, 0.25 mmol) in THF was added phenylsilane (334 μl, 2.71 mmol). The mixture was stirred at room temperature overnight under nitrogen, THF was evaporated off the mixture and the residue was purified by flash chromatography (hexane/EtOAc, 20/80) to afford the title compound 123 (881 mg, 98%). 1H-NMR (DMSO) δ: 8.00 (d, J=1.0 Hz, 1H), 7.70 (d, J=8.2 Hz, 1H); 7.58 (dd, J=8.4, 1.6 Hz, 1H); 7.52 (d, J=2.0 Hz, 1H); 6.70 (d, J=9.0 Hz, 2H); 6.59 (d, J=9.0 Hz, 2H); 5.48 (t, J=5.8 Hz, 1H); 4.31 (d, J=5.7 Hz, 2H); 3.83 (s, 3H); 3.68 (t, J=4.7 Hz, 4H); 2.86 (t, J=4.7 Hz, 4H).

후처리

  1. customTHF was evaporated off the mixture
  2. customthe residue was purified by flash chromatography (hexane/EtOAc, 20/80)

출처 및 근거

ORD 기록
ord-a93867ec299d407ea2aeea786393e51a
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088805B2

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