2-Bromothiazole → 2-(4-Fluorophenyl)thiazole

HRID 1777428Notes

Reaction equation

HRID 1777428 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=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:3][CH:4]=[CH:5][N:6]=2)=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 764302-BromothiazoleHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 105117252-(4-Fluorophenyl)thiazole

Procedure

Using 2-bromothiazole (5.0 g, 30.482 mmol) and (4-fluorophenyl)boronic acid (8.528 g, 60.964 mmol) as reactants and following the procedure described in Example 7 step 1, the title compound was obtained after purification by flash chromatography (60-120μ; 4% ethyl acetate in hexane) as colorless liquid (5.0 g, 91% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.00-7.89 (m, 2H), 7.90 (d, 1H), 7.76 (d, 1H), 7.32 (t, 2H); LC-MS m/z calculated for [M+H]+ 180.02. found 180.1.

Sources & evidence

ORD record
ord-eb5815163d7a4c85ac662969d9a0b672
Source dataset
uspto-grants-2016_02
Patent number
US09266873B2

Reaction notes

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