Diisopropylethylamine → 2-Bromo-6-(4-fluoro-phenyl)-imidazo[2,1-b]thiazole

HRID 659147Notes

Reaction equation

HRID 659147 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.Br.[Br:13][C:14]1[S:18][C:17]([NH2:19])=[N:16][CH:15]=1.C(N(C(C)C)C(C)C)C>C(O)C>[Br:13][C:14]1[S:18][C:17]2=[N:19][C:3]([C:5]3[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=3)=[CH:2][N:16]2[CH:15]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 27238485-Bromothiazol-2-amine monohydrobromide

Product 1

HCID 249907052-Bromo-6-(4-fluoro-phenyl)-imidazo[2,1-b]thiazoleYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-bromo-1-(4-fluoro-phenyl)-ethanone (2 g, 9.215 mmol) in 100 ml ethanol were added 5-bromo-thiazol-2-ylamine hydrobromide (2.396 g, 9.215 mmol) and ethyl-diisopropyl-amine (1.19 g, 9.215 mmol). The mixture was stirred under reflux for 8 h and evaporated. Water was added to the residue and extracted with ethyl acetate. The organic layer was separated, washed with water, dried and evaporated. The crude product was purified by preparative HPLC (RP18, acetonitrile/water 0.1% TFA) to yield 532 mg (20%) of the desired product. MS: M+H+=296.96.

Workup

  1. temperatureunder reflux for 8 h
  2. customevaporated
  3. additionWater was added to the residue
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water
  7. customdried
  8. customevaporated
  9. customThe crude product was purified by preparative HPLC (RP18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-b9985385d8914badabdf7317b20ca8bc
Source dataset
uspto-grants-2011_12
Patent number
US08080569B2

Reaction notes

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