Potassium Carbonate → 2-(4-Bromophenyl)-4-{2-[(3R)-3-fluoropyrrolidin-1-yl]ethyl}-5-methyl-1,3-oxazole

HRID 1445843Notes

Reaction equation

HRID 1445843 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:20])=[C:11]([CH2:13][CH2:14]OS(C)(=O)=O)[N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O)(=O)=O)=CC=1.[F:38][C@@H:39]1[CH2:43][CH2:42][NH:41][CH2:40]1>[I-].[K+].C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:20])=[C:11]([CH2:13][CH2:14][N:41]3[CH2:42][CH2:43][C@@H:39]([F:38])[CH2:40]3)[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11451238Methanesulfonic acid 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl ester2×HCID 86614634(3R)-3-Fluoropyrrolidine 4-methylbenzenesulfonate

Product 1

HCID 117100882-(4-Bromophenyl)-4-{2-[(3R)-3-fluoropyrrolidin-1-yl]ethyl}-5-methyl-1,3-oxazoleYield 102.9%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

Prepare using the method of Example 102 with 2-[2-(4-bromophenyl)-5-methyl-1,3-oxazol-4-yl]ethyl methanesulfonate (See Intermediate 13) (0.16 g, 0.44 mmole), anhydrous acetonitrile (2 mL), potassium carbonate (0.21 g, 1.54 mmol), potassium iodide (0.007 g, 0.04 mmol) and (3R)-3-fluoropyrrolidine 4-methylbenzenesulfonate (salt) (See Intennediate 51) (0.21 g, 0.79 mmol) to give the title compound as a pale orange oil (0.16 g): MS (m/e) (79Br/81Br): 353, 355(M+1)

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-3fc938fb63e94c3e9b0d0e4bbaf6273e
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

Loading…