Potassium Carbonate → HCID 11530378, compound

HRID 1445857Notes

Reaction equation

HRID 1445857 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+].Cl.[CH3:28][C@@H:29]1[CH2:33][CH2:32][CH2:31][NH:30]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:30]3[CH2:31][CH2:32][CH2:33][C@H:29]3[CH3:28])[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11147704(2R)-(-)-2-Methylpyrrolidine hydrochloride2×HCID 11451238Methanesulfonic acid 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl ester2×

Product 1

HCID 11530378HCID 11530378, compoundYield 103.4%

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) (0.65 g, 1.80 mmole), anhydrous acetonitrile (6 mL), potassium carbonate (0.87 g, 6.32 mmol), potassium iodide (0.03 g, 0.18 mmol) and (2R)-2-methylpyrrolidine hydrochloride (salt) (See Intermediate 7) (0.25 g, 2.08 mmol) to give the title compound as a pale orange oil (0.65 g): MS (m/e) (79Br/81Br): 349, 351(M+1)

Workup

  1. customPrepare

Sources & evidence

ORD record
ord-31bb789d1f0141f696fe70930290060f
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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