Hydrochloric Acid → HCID 89579710, compound

HRID 2276809Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:27]=[CH:26][C:12]([O:13][C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:15]=3)=[CH:11][CH:10]=2)O1.Cl[C:30]1[N:35]=[C:34]([C:36]([OH:38])=[O:37])[CH:33]=[C:32]([CH:39]=[CH2:40])[N:31]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>COCCOC.CCO.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([O:13][C:12]2[CH:11]=[CH:10][C:9]([C:30]3[N:35]=[C:34]([C:36]([OH:38])=[O:37])[CH:33]=[C:32]([CH:39]=[CH2:40])[N:31]=3)=[CH:27][CH:26]=2)=[CH:15][C:16]=1[C:22]([F:25])([F:24])[F:23])#[N:19]

Participants

Conditions

Temperature: 90 °C

Procedure

A 100 mL round bottom flask was charged with 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-2-(trifluoromethyl)benzonitrile (1.5 g, 3.86 mmol), 2-chloro-6-vinylpyrimidine-4-carboxylic acid (709.5 mg, 3.86 mmol), PdCl2(PPh3)2 (190 mg, 0.27 mmol), and cesium carbonate (2.5 g, 7.72 mmol) in DME (8 mL), EtOH (4 mL), and water (8 mL). The reaction mixture was heated to 90° C. for 10 hours. The reaction mixture was diluted with 100 mL water, acidified to pH 5 with aqueous 4N HCl, and extracted with 2×100 mL EtOAc. The combined organic layers were dried over sodium sulfate and concentrated to give 2-(4-(4-cyano-3-(trifluoromethyl)phenoxy)phenyl)-6-vinylpyrimidine-4-carboxylic acid as a light brown solid. The material was used in the next step without purification. LC/MS: m/z=412 [M+H]+.

Workup

extractionextracted with 2×100 mL EtOAc
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-591ec9bec9764fa99006dd2cf94f7595
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133131B2

Reaction notes

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