2-Naphthalenesulfonyl chloride → HCID 9824069, compound

HRID 635935Notes

Reaction equation

HRID 635935 reaction equation
[CH2:1]1[CH:9]2[N:4]([CH2:5][CH2:6][CH: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.[C:19]1([S:29](Cl)(=[O:31])=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1C2C(=CC=CC=2)C=CC=1S(Cl)(=O)=O>C1COCC1>[CH2:1]1[CH:9]2[N:4]([CH2:5][CH2:6][CH:7]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[N:16][CH:17]=4)[N:12]([S:29]([C:19]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH:22]=[CH:21][CH:20]=4)(=[O:31])=[O:30])[CH:11]=3)[CH2:8]2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 71252-Naphthalenesulfonyl chlorideHCID 665601-Naphthalenesulfonyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amide2×HCID 9837669HCID 9837669, compound2×

Product 1

HCID 9824069HCID 9824069, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

from 3-(octahydro-7-indolizinyl)-1-H-5-azaindole (10 mg, 0.0415 mmol), 1-naphthalenesulfonyl chloride (15 mg, 0.072 mmol) and 1M NaN(TMS)2 (100 μL, 0.10 mmol) in THF (0.5 mL) at RT. The two enantiomers were separated by Chiral chromatography (Chiracel OD). 3-(Octahydro-7-indolizinyl)-1-(2-naphthalenesulfonyl)-5-azaindole (17.5 mg, 97.7%); from 3-(octahydro-7-indolizinyl)-1-H-5-azaindole (10 mg, 0.0415 mmol), 2-naphthalenesulfonyl chloride (15 mg, 0.072 mmol) and 1M NaN(TMS)2 (100 μL, 0.10 mmol) in THF (0.5mL) at RT.

Workup

  1. customat RT
  2. customThe two enantiomers were separated by Chiral chromatography (Chiracel OD)
  3. customat RT

Sources & evidence

ORD record
ord-5cb5b8008ec54ae1b613f73b68099323
Source dataset
uspto-grants-2001_02
Patent number
US06191141B1

Reaction notes

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