Potassium Carbonate → HCID 11646016, compound

HRID 1445845Notes

Reaction equation

HRID 1445845 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+].[NH:27]1[CH2:31][CH2:30][C@@H:29]([OH:32])[CH2:28]1.CC1C=CC(S([O-])(=O)=O)=CC=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:27]3[CH2:31][CH2:30][C@@H:29]([OH:32])[CH2:28]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 131727894HCID 131727894, compound2×

Product 1

HCID 11646016HCID 11646016, compoundYield 97.1%

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)-pyrrolidin-3-ol 4-methylbenzenesulfonate (salt) (See Intermediate 52) (0.13 g, 0.51 mmol) to give the title compound as a pale orange oil (0.15 g): MS (m/e) (79Br/81Br): 351, 353(M+1)

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-00b06536b6074ad3971659a26257556e
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

Loading…