Benzyl Bromide → 6-Dibenzylamino-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 545464Notes

Reaction equation

HRID 545464 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]2[CH:6]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[S:8][C:4]=2[CH:3]=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:12][O:11][C:9]([C:7]1[S:8][C:4]2[CH:3]=[C:2]([N:1]([CH2:6][C:5]3[CH:13]=[CH:14][CH:2]=[CH:3][CH:4]=3)[CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:14]=[CH:13][C:5]=2[CH:6]=1)=[O:10]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 15557582Methyl 6-aminobenzo[b]thiophene-2-carboxylate

Product 1

HCID 589690636-Dibenzylamino-benzo[b]thiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 6-aminobenzothiophene-2-carboxylate (29 mg, 0.140 mmol) was dissolved in 1 mL of anhydrous DMF and reacted with benzyl bromide (40 μL, 0.38 mmol) in the presence of potassium carbonate (41 mg, 0.30 mmol) at 80° C. under a nitrogen atmosphere for 16 h. The reaction mixture was used in the next step without further purification. MS (EI): cal'd 388 (MH+), exp 388 (MH+).

Workup

  1. customThe reaction mixture was used in the next step without further purification

Sources & evidence

ORD record
ord-8995d6cc590c4da5ae172e52abf823aa
Source dataset
uspto-grants-2011_05
Patent number
US07935724B2

Reaction notes

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