Benzenesulfonyl chloride → 3-(Octahydro-7-indolizinyl)-1-benzenesulfonyl-7-azaindole

HRID 2119556Notes

Reaction equation

HRID 2119556 reaction equation
[CH2:1]1[CH:9]2[N:4]([CH2:5][CH2:6][CH: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.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[CH2:1]1[CH:9]2[N:4]([CH2:5][CH2:6][CH:7]([C:10]3[C:18]4[C:13](=[N:14][CH:15]=[CH:16][CH:17]=4)[N:12]([S:25]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)(=[O:27])=[O:26])[CH:11]=3)[CH2:8]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 102204153-(octahydro-7-indolizinyl)-1H-7-azaindole

Product 1

HCID 98647333-(Octahydro-7-indolizinyl)-1-benzenesulfonyl-7-azaindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

from 3-(octahydro-7-indolizinyl)-1H-7-azaindole (less polar isomer) (10 mg, 0.0415 mmol), benzenesulfonyl chloride (10 μL, 0.0784 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-9d5b4181c7b54a9cb3a5d860635aa68a
Source dataset
uspto-grants-2004_02
Patent number
US06686374B1

Reaction notes

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