2-Cyanophenylboronic acid → HCID 86679855, compound

HRID 1519362Notes

Reaction equation

HRID 1519362 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)[N:14]=2)[CH:7]=[CH:6][C:5]=1Br.[C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O)#[N:26]>>[C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:5]1[C:4]([C:3]([OH:2])=[O:24])=[CH:9][C:8]([C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)[N:14]=2)=[CH:7][CH:6]=1)#[N:26]

Participants

3

Reactant 2

HCID 27346102-Cyanophenylboronic acidHCID 86679833Methyl 2-bromo-5-(4-(3,4-dichlorophenyl)thiazol-2-yl)benzoate2×

Product 1

HCID 86679855HCID 86679855, compoundYield 2.2%

Procedure

Using the conditions of General Procedure B for Suzuki Coupling and Hydrolysis in Parallel Mode, 2-bromo-5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-benzoic acid methyl ester (which may be prepared as described for Intermediate 6; 89 mg, 0.2 mmol) was reacted with 2-cyanophenylboronic acid (available from Aldrich Chemical Company, Inc.; 59 mg, 0.4 mmol). The resulting ester was hydrolyzed and the acid was purified to give 2′-cyano-4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2-carboxylic acid (2 mg, 1%). The compound of Example 111 has the same formula as the compound of Example 112. LCMS analysis indicated that the material was ˜94% pure, as measured by UV at 214 nm. LRMS m/z 450.8 (M+H+).

Workup

  1. customthe acid was purified

Sources & evidence

ORD record
ord-7431809271424aa7854ece7211d62fd1
Source dataset
uspto-grants-2015_07
Patent number
US09073881B2

Reaction notes

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