2-Chloromethyl 2-(trimethylsilyl)ethyl ether → HCID 58656455, compound

HRID 1988903Notes

Reaction equation

HRID 1988903 reaction equation
CC(C)([O-])C.[Na+].[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)(=[O:19])=[O:18])=[N:13][NH:14]2)=[CH:10][CH:9]=1.[CH3:27][Si:28]([CH3:35])([CH3:34])[CH2:29][CH2:30][O:31][CH2:32]Cl>O1CCCC1>[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([S:17]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)(=[O:19])=[O:18])=[N:13][N:14]2[CH2:32][O:31][CH2:30][CH2:29][Si:28]([CH3:35])([CH3:34])[CH3:27])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 23676156Sodium t-butoxideHCID 178527357HCID 178527357, compound2×

Product 1

HCID 58656455HCID 58656455, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium tert-butoxide (0.035 g) was added to an ice-cold solution of 6-bromo-3-[(4-fluorophenyl)sulfonyl]-1H-indazole (Intermediate 69) (0.11 g) in tetrahydrofuran (1.5 ml). 2-(Trimethylsilyl)ethoxymethyl chloride (0.06 ml) was then added and the mixture was warmed to room temp. over 1 h. The reaction was quenched using 2M aqueous ammonia (1 ml) and methanol (1 ml) the solvent was evaporated and the residue was purified on a Varian Bond-Elut SPE cartridge, eluting with cyclohexane:dichloromethane (100:0 to 0: 100) to give the title compound (0.67 g).

Workup

  1. temperaturethe mixture was warmed to room temp. over 1 h
  2. customThe reaction was quenched
  3. customwas evaporated
  4. customthe residue was purified on a Varian Bond-Elut SPE cartridge
  5. washeluting with cyclohexane:dichloromethane (100:0 to 0: 100)

Sources & evidence

ORD record
ord-41c6dab343734682aa42ac3cc7c2473d
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

Loading…