Benzyl Bromide → 5-Dibenzylamino-benzo[b]thiophene-2-carboxylic acid ethyl ester

HRID 545463Notes

Reaction equation

HRID 545463 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][C:6]=2[CH:15]=1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C(=O)(O)[O-].[Na+]>[CH2:13]([O:12][C:10]([C:8]1[S:9][C:5]2[CH:4]=[CH:3][C:2]([N:1]([CH2:7][C:6]3[CH:15]=[CH:2][CH:3]=[CH:4][CH:5]=3)[CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][C:6]=2[CH:7]=1)=[O:11])[CH3:14]

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2764450Ethyl 5-amino-1-benzothiophene-2-carboxylate

Product 1

HCID 589689785-Dibenzylamino-benzo[b]thiophene-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Ethyl 5-aminobenzothiophene -2-carboxylate (74 mg, 0.344 mmol) was dissolved in 1 mL of anhydrous DMF and reacted with benzyl bromide (100 μL, 0.84 mmol) in the presence of potassium carbonate (97 mg, 0.70 mmol) at 80° C. under a nitrogen atmosphere for 16 h. The reaction mixture was diluted with water and sat. sodium bicarbonate and extracted with ethyl acetate. The organic phase was dried over sodium sulfate. The solvent was removed under reduced pressure and the crude left under high vacuum overnight. It was used in the next step without further purification. MS (EI): cal'd 402 (MH+), exp 402 (MH+).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customIt was used in the next step without further purification

Sources & evidence

ORD record
ord-7a1ffeaafc38407eb31d7c8fe56cfde5
Source dataset
uspto-grants-2011_05
Patent number
US07935724B2

Reaction notes

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