4-Toluenesulfonyl chloride → 3-(1,2,3,5,8,8a-Hexahydro-7-indolizinyl)-1-(4-methylbenzenesulfonyl)-5-azaindole

HRID 635931Notes

Reaction equation

HRID 635931 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.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[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)[N:12]([S:26]([C:23]4[CH:24]=[CH:25][C:20]([CH3:19])=[CH:21][CH:22]=4)(=[O:28])=[O:27])[CH:11]=3)[CH2:8]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 101309743-(1,2,3,5,8,8a-hexahydro-7-indolizinyl)-1H-5-Azaindole

Product 1

HCID 99524883-(1,2,3,5,8,8a-Hexahydro-7-indolizinyl)-1-(4-methylbenzenesulfonyl)-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), 4-methyl-benzenesulfonyl chloride (20 mg, 0.105 mmol) and 1M NaN(TMS)2 (100 μL, 0.10 mmol) in THF (0.5 mL) at RT.

Workup

  1. customat RT

Sources & evidence

ORD record
ord-1ab1f07da5de4576a276e4f14e7b3764
Source dataset
uspto-grants-2001_02
Patent number
US06191141B1

Reaction notes

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