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

HRID 852923Notes

Reaction equation

HRID 852923 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-563ab341e63f457d819162dd507385d2
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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