Cesium carbonate → HCID 86699630, compound

HRID 68325Notes

Reaction equation

[OH:1][N:2]=[CH:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]=2)[NH:6][CH:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:26][C:27]([F:37])([F:36])[C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=1>CN(C=O)C>[F:26][C:27]([F:37])([F:36])[C:28]1[CH:35]=[CH:34][C:31]([CH2:32][N:6]2[C:7]3[C:12](=[CH:11][C:10]([O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=3)[C:4]([CH:3]=[N:2][O:1][CH2:32][C:31]3[CH:30]=[CH:29][C:28]([C:27]([F:26])([F:36])[F:37])=[CH:35][CH:34]=3)=[CH:5]2)=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of the product of step 3 (280 mg, 1.068 mmoles) in DMF (2 ml), cesium carbonate (1.0 gm, 3.2 mmoles), 4-trifluoromethyl benzylbromide (510 mg, 2.13 mmoles were added and the reaction mixture was stirred at 25° C. for 2 hours. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The combined ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evaporated under reduced pressure, The crude product was purified by column chromatography using 15% EtOAC in hexane as eluent to yield 350 mg (56%) of product as solid.

Workup

additionThe reaction mixture was poured into ice cold water
extractionextracted with ethyl acetate
extractionThe combined ethyl acetate extract
washwas washed with water & brine
dry with materialdried over sodium sulphate
customevaporated under reduced pressure
customThe crude product was purified by column chromatography

Sources & evidence

ORD record: ord-abfd650c8a694cad87e60efabc5374fc
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822414B2

Reaction notes

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