Potassium Carbonate → Methyl 4-(5-methyl-4-((4-(trifluoromethyl)phenylsulfonyl)methyl)oxazol-2-yl)benzoate

HRID 931529Notes

Reaction equation

[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[Li+].Cl[CH2:16][C:17]1[N:18]=[C:19]([C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=2)[O:20][C:21]=1[CH3:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:22][C:21]1[O:20][C:19]([C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=2)=[N:18][C:17]=1[CH2:16][S:9]([C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:12])[F:13])=[CH:8][CH:7]=1)(=[O:11])=[O:10]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of lithium 4-(trifluoromethyl)benzenesulfinate (700 mg, 3.24 mmol, 1.72 equiv, 100%), methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate (500 mg, 1.89 mmol, 1.00 equiv) and potassium carbonate (0.35 g) in N,N-dimethylformamide (25 mL) was stirred overnight at 70° C. The reaction mixture was cooled to room temperature then quenched by the addition of 60 mL of water and ice. The solid was collected by filtration, washed with 2×20 mL of water and dried in a vacuum oven to yield 0.7 g (85%) of methyl 4-(5-methyl-4-((4-(trifluoromethyl)phenylsulfonyl)methyl)oxazol-2-yl)benzoate as a white solid. LC-MS: (ES, m/z): 481 [M+CH3CN+H]+, 440 [M+H]+, 271, 146, 105.

Workup

temperatureThe reaction mixture was cooled to room temperature
customthen quenched by the addition of 60 mL of water and ice
filtrationThe solid was collected by filtration
washwashed with 2×20 mL of water
customdried in a vacuum oven

Sources & evidence

ORD record: ord-16cd8b06e0b14350becd4e5f63f1e08a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296732B2

Reaction notes

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