4-Fluorophenylboronic acid → 5-(4-Fluorophenyl)thiazole

HRID 1777442Notes

Reaction equation

HRID 1777442 reaction equation
Br[C:2]1[S:6][CH:5]=[N:4][CH:3]=1.[F:7][C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1>>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:2]2[S:6][CH:5]=[N:4][CH:3]=2)=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 5460595-Bromothiazole

Product 1

HCID 217096515-(4-Fluorophenyl)thiazole

Procedure

Using 5-bromothiazole (1.0 g, 6.09 mmol) and (4-fluorophenyl)boronic acid (1.0 g, 7.31 mmol) and following the procedure described in example 7 step 1, the title compound was obtained after purification by purified by Biotage IsoleraOne® column (10% ethyl acetate in hexane) as yellow viscous liquid (0.4 g, 36% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.05 (s, 1H), 8.25 (s, 1H), 7.73-7.69 (m, 2H), 7.27 (t, 2H); LC-MS m/z calculated for [M+H]+ 180.02. found 180.1.

Sources & evidence

ORD record
ord-2b8989cc7c9f428da2cd5c7672c3e7f0
Source dataset
uspto-grants-2016_02
Patent number
US09266873B2

Reaction notes

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