2-Bromoethanol → HCID 118060618, compound

HRID 2274808Notes

Reaction equation

HRID 2274808 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:21]=[N:22][NH:23][CH:24]=3)=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.Br[CH2:26][CH2:27][OH:28].C([O-])([O-])=O.[K+].[K+]>CC#N>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:24]=[N:23][N:22]([CH2:26][CH2:27][OH:28])[CH:21]=3)=[CH:7][N:8]2[S:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:12])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 1180601346-fluoro-1-(phenylsulfonyl)-3-(1H-pyrazol-4-yl)-1H-indole2×

Product 1

HCID 118060618HCID 118060618, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6-fluoro-1-(phenylsulfonyl)-3-(1H-pyrazol-4-yl)-1H-indole (Intermediate 5; 1.20 mg; 0.35 mmol), 2-bromoethanol (157 mg; 1.26 mmol) and K2CO3 (145 mg; 1.05 mmol) in MeCN (4 mL) was heated to 165° C. for 1 h in a microwave reactor. The reaction mixture was filtered and washed with MeCN. The combined filtrate was concentrated and purified by preparative TLC (petroleum ether/EtOAc=1/1) to afford 41 mg (30%) of the title compound as a yellow semi-solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with MeCN
  3. concentrationThe combined filtrate was concentrated
  4. custompurified by preparative TLC (petroleum ether/EtOAc=1/1)

Sources & evidence

ORD record
ord-ed6502b78a144420b1100c08c6ddba46
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

Loading…