4-Fluorobenzenesulfonyl chloride → HCID 9865565, compound

HRID 895435Notes

Reaction equation

HRID 895435 reaction equation
[CH2:1]1[CH:9]2[N:4]([CH2:5][CH:6]=[C:7]([C:10]3[C:18]4[C:13](=[N:14][CH:15]=[CH:16][CH:17]=4)[NH:12][CH:11]=3)[CH2:8]2)[CH2:3][CH2:2]1.[F: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>[F:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][N:14]=3)[C:10]([C:7]3[CH2:8][CH:9]4[N:4]([CH2:3][CH2:2][CH2:1]4)[CH2:5][CH:6]=3)=[CH:11]2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 10220373HCID 10220373, compound

Product 1

HCID 9865565HCID 9865565, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Chlorobenzenesulfonyl)-3-(1,2,3,5,8,8a-hexahydro-7-indolizinyl-7-azaindole (10.2 mg, 58.9%); from 3-(1,2,3,5,8,8a-hexahydro-7-indolizinyl)-1H-7-Azaindole (10 mg, 0.0418 mmol), 4-fluorobenzenesulfonyl chloride (20 mg, 0.095 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-6068b53efb46479ca010245eb9c42051
Source dataset
uspto-grants-2005_07
Patent number
US06916818B2

Reaction notes

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