2-Bromothiazole → HCID 22473555, compound

HRID 2184046Notes

Reaction equation

HRID 2184046 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]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1B1OC(C)(C)C(C)(C)O1>>[F:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[C:2]1[S:3][CH:4]=[CH:5][N:6]=1

Participants

3

Reactant 2

HCID 764302-BromothiazoleHCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol ester

Product 1

HCID 22473555HCID 22473555, compound

Procedure

2-Bromothiazole (2.1 ml, 22.9 mmol) was coupled to 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (3.0 g, 11.6 mmol) using the method in Example 47. Purification by chromatography on silica gel eluting with dichloromethane then recrystallisation from toluene/isohexane gave 2-(2-fluoro-5-nitrophenyl)thiazole as a brown solid: δH (360 MHz, CDCl3) 7.38 (1H, t, J 9), 7.58 (1H, d, J 3), 8.03 (1H, t, J 3), 8.26-8.31 (1H, m), 9.26 (1H, d, J 6 and 3).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane
  2. customrecrystallisation from toluene/isohexane

Sources & evidence

ORD record
ord-66c8edcb85f4442d89b1052d91cdf851
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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