Phenylboronic Acid → HCID 4347548, compound

HRID 1191953Notes

Reaction equation

HRID 1191953 reaction equation
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][C:4]([C:7]2[S:8][C:9](Br)=[CH:10][N:11]=2)=[CH:3][CH:2]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][C:4]([C:7]2[S:8][C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:10][N:11]=2)=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 86691022HCID 86691022, compound

Product 1

HCID 4347548HCID 4347548, compoundYield 98%

Procedure

The compound of the title was prepared in a similar way to example 3 from 2-(biphenyl-4-yl)-5-bromothiazole (311 mg, 0.98 mmol) and phenylboronic acid (955 mg, 1.27 mmol) for 4 h at 100° C. Flash chromatography of the residue on silica gel (SiO2, hexane:ethyl acetate, 8:2) afforded 300 mg of 2-(biphenyl-4-yl)-5-phenylthiazole as a white solid (98% yield). EM (IE): m/z (%): 313; (M+, 100). HRMS (ESI): (M+H)+: calculated for C21H15NS: 314.0925. found: 314.0995.

Sources & evidence

ORD record
ord-16c246c55ef24bea8dc430513f976b54
Source dataset
uspto-grants-2014_03
Patent number
US08680126B2

Reaction notes

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