4-Fluorobenzoyl chloride → Ethyl 2-bromo-5-(4-fluorobenzamido)-thiazole-4-carboxylate

HRID 512543Notes

Reaction equation

HRID 512543 reaction equation
[NH2:1][C:2]1[S:6][C:5]([Br:7])=[N:4][C:3]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[Br:7][C:5]1[S:6][C:2]([NH:1][C:18](=[O:19])[C:17]2[CH:21]=[CH:22][C:14]([F:13])=[CH:15][CH:16]=2)=[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:4]=1

Participants

5

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 59355801Ethyl 5-amino-2-bromothiazole-4-carboxylate

Product 1

HCID 86703378Ethyl 2-bromo-5-(4-fluorobenzamido)-thiazole-4-carboxylateYield 94.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent2×

Procedure

To a mixture of ethyl 5-amino-2-bromothiazole-4-caboxylate (0.50 g, 1.99 mmol) and a catalytic amount of DMAP in pyridine (5 mL) was added a solution of 4-fluorobenzoyl chloride (0.377 g, 2.39 mmol) in pyridine (5 mL) at 0° C. The mixture was allowed to warm to rt, and stirred for 16 hrs. The reaction mixture was quenched with ice-water, and the resulting solids were collected. The solids were purified by silica gel column chromatography eluted with 20% EtOAc in hexane to give 0.70 g (93% yield) of the title compound.

Workup

  1. customThe reaction mixture was quenched with ice-water
  2. customthe resulting solids were collected
  3. customThe solids were purified by silica gel column chromatography
  4. washeluted with 20% EtOAc in hexane

Sources & evidence

ORD record
ord-6cf34a9f82384efa9e68097507796ddc
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Reaction notes

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