Acetic Anhydride → N-(2-(4-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)ethyl)acetamide

HRID 2274805Notes

Reaction equation

HRID 2274805 reaction equation
Cl.[F:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:21]3[CH:22]=[N:23][N:24]([CH2:26][CH2:27][NH2:28])[CH:25]=3)=[CH:8][N:9]2[S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:5][CH:4]=1.[CH3:29][C:30](OC(C)=O)=[O:31]>N1C=CC=CC=1>[F:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:21]3[CH:22]=[N:23][N:24]([CH2:26][CH2:27][NH:28][C:30](=[O:31])[CH3:29])[CH:25]=3)=[CH:8][N:9]2[S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:14])=[O:13])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 1180602982-(4-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)ethanamine hydrochloride2×

Product 1

HCID 118060269N-(2-(4-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)ethyl)acetamideYield 56.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the solution of 2-(4-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)ethanamine hydrochloride (Intermediate 19; 260 mg; 0.62 mmol) in pyridine (3 mL), was added Ac2O (2.00 mL; 2.13 mmol) under nitrogen. The reaction mixture was stirred overnight. The reaction mixture was concentrated and the residue was trituated with a small amount of EtOAc to afford 150 mg (52%) of the title compound as a red solid, which was used directly without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-bb882f64201c46cf854c2fa8f835cce7
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

Loading…