Cesium fluoride → HCID 10195159, compound

HRID 854560Notes

Reaction equation

C([O:3][C:4](=[O:33])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[S:19][C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[N:17][C:16]=2[CH2:30][CH3:31])=[C:9]([CH3:32])[CH:8]=1)C.C(OC(=O)COC1C=CC(OCC2SC(C3C=CC(C(F)(F)F)=CC=3)=NC=2CC)=C(Br)C=1)C.CB(O)O.[F-].[Cs+]>O1CCOCC1.C(Cl)Cl>[CH2:30]([C:16]1[N:17]=[C:18]([C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:25]=2)[S:19][C:15]=1[CH2:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:33])=[O:3])=[CH:8][C:9]=1[CH3:32])[CH3:31]

Participants

Conditions

Temperature: 80 °C

Procedure

{4-[4-Ethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-3-methyl-phenoxy}-acetic acid ethyl ester To a mixture of {3-Bromo-4-[4-ethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenoxy}-acetic acid ethyl ester (100 mg, 0.18 mmol), methyl boronic acid (33 mg, 0.54 mmol) and cesium fluoride (90 mg, 0.54 mmol) in dioxane (2 mL) is added [1,1′]-(bisdiphenylphosphino)ferrocene]-dichloridepalladium (II) complex with methylene chloride (1:1, 29 mg) under nitrogen. The mixture is heated to 80° C. for 18 hrs, cooled to room temperature, loaded on silica gel column. Chromatography gave the title compound (80 mg).

Workup

temperaturecooled to room temperature

Sources & evidence

ORD record: ord-80de825bf6a541aebdc71d0acda154fa
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259175B2

Reaction notes

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