2,6-Dimethoxybenzoyl chloride → 1-(2,6-Dimethoxylbenzoyl)-3-(1,2,3,5,8,8a-hexahydro-7-indolizinyl)-5-azaindole

HRID 635929Notes

Reaction equation

HRID 635929 reaction equation
[CH2:1]1[CH:9]2[N:4]([CH2:5][CH:6]=[C:7]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[N:16][CH:17]=4)[NH:12][CH:11]=3)[CH2:8]2)[CH2:3][CH2:2]1.[O:19]([C:21]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[C:22]=1[C:23](Cl)=[O:24])[CH3:20].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[O:19]([C:21]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[C:22]=1[C:23]([N:12]1[C:13]2[C:18](=[CH:17][N:16]=[CH:15][CH:14]=2)[C:10]([C:7]2[CH2:8][CH:9]3[N:4]([CH2:3][CH2:2][CH2:1]3)[CH2:5][CH:6]=2)=[CH:11]1)=[O:24])[CH3:20]

Participants

5

Reactant 3

HCID 748102,6-Dimethoxybenzoyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 101309743-(1,2,3,5,8,8a-hexahydro-7-indolizinyl)-1H-5-Azaindole

Product 1

HCID 98013061-(2,6-Dimethoxylbenzoyl)-3-(1,2,3,5,8,8a-hexahydro-7-indolizinyl)-5-azaindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

from 3-(1,2,3,5,8,8a-hexahydro-7-indolizinyl)-1H-5-Azaindole (10 mg, 0.0418 mmol), 2,6-dimethoxylbenzoyl chloride (20 mg, 0.0997 mmol) and 1M NaN(TMS)2 (100 μL, 0.10 mmol) in THF (1 mL) at RT.

Workup

  1. customat RT

Sources & evidence

ORD record
ord-29d4f2f00a33437aaa1cb3f0b7b87068
Source dataset
uspto-grants-2001_02
Patent number
US06191141B1

Reaction notes

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