2,6-Dichlorobenzoyl chloride → 1-(2,6-Dichlorobenzoyl)-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-5-azaindole

HRID 635940Notes

Reaction equation

HRID 635940 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[N:14][CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1.[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:19]=1[C:20](Cl)=[O:21].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:19]=1[C:20]([N:10]1[C:11]2[C:16](=[CH:15][N:14]=[CH:13][CH:12]=2)[C:8]([C:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH:6]=2)=[CH:9]1)=[O:21]

Participants

5

Reactant 3

HCID 783922,6-Dichlorobenzoyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 97943653-(1-Methyl-1,2,3,6-tetrahydro-4-pyridinyl)-5-azaindole

Product 1

HCID 98003201-(2,6-Dichlorobenzoyl)-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-5-azaindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

from 3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)5-azaindole (20 mg, 0.094 mmol), 2,6-dichlorobenzoyl chloride (27 μL, 0.188 mmol) and 1M NaN(TMS)2 (250 μL, 0.25 mmol) in THF (1 mL) at RT.

Workup

  1. customat RT

Sources & evidence

ORD record
ord-c59ccdb5b6954c15b3a3c196bd15545e
Source dataset
uspto-grants-2001_02
Patent number
US06191141B1

Reaction notes

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