3-(Bromomethyl)-5-chloro-1-benzothiophene → HCID 59176754, compound

HRID 215976Notes

Reaction equation

HRID 215976 reaction equation
Br.[N:2]1[C:3](=[O:11])[CH2:4][N:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=12.Br[CH2:13][C:14]1[C:15]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:16]=2[S:17][CH:18]=1>C1COCC1>[Cl:23][C:21]1[CH:20]=[CH:19][C:16]2[S:17][CH:18]=[C:14]([CH2:13][CH:4]3[N:5]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]4=[N:2][C:3]3=[O:11])[C:15]=2[CH:22]=1

Participants

4

Reactant 2

HCID 27798573-(Bromomethyl)-5-chloro-1-benzothiopheneHCID 44121307Imidazo[1,2-a]pyridin-2(3H)-one--hydrogen bromide (1/1)

Product 1

HCID 59176754HCID 59176754, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 100 mg (0.47 mmol) of imidazo[1,2-a]pyridin-2-one hydrobromide salt and 122 mg (0.47 mmol) 3-bromomethyl-5-chloro-benzo[b]thiophene in 5 mL of THF is treated with 1 mL (1.0 mmol) of 1M lithium bis(trimethylsilyl)amide THF solution at −78° C. The resulting mixture is stirred this temperature for 1 h and the mixture is quenched with saturated ammonium chloride solution. The product is extracted with ethyl acetate. The organic layer is washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography to give the desired compound.

Workup

  1. customthe mixture is quenched with saturated ammonium chloride solution
  2. extractionThe product is extracted with ethyl acetate
  3. washThe organic layer is washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-cf3469b4829544b29c2a2d2397c5ce5f
Source dataset
uspto-grants-2012_06
Patent number
US08193214B2

Reaction notes

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