Methyl 3-(bromomethyl)thiophene-2-carboxylate → Methyl 3-(aminomethyl)thiophene-2-carboxylate

HRID 1924968Notes

Reaction equation

HRID 1924968 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[CH2:10]Br)=[O:4].CO.[NH3:14]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[CH2:10][NH2:14])=[O:4]

Participants

4

Reactant 2

HCID 10537693Methyl 3-(bromomethyl)thiophene-2-carboxylateHCID 21705897Ammonia methanol

Product 1

HCID 53419606Methyl 3-(aminomethyl)thiophene-2-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Bromomethyl-thiophene-2-carboxylic acid methyl ester (1.297 g, 5.54 mmol) is dissolved in DMF (30 mL) and MeOH/NH3 is added (30 mL). The reaction mixture is stirred at room temperature for 1 hour, and concentrated in vacuo. Purification of the residue by silica gel column chromatography eluting with 95:5 and 93:7 DCM:MeOH affords the title compound (0.82 g, 86%).

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification of the residue by silica gel column chromatography
  3. washeluting with 95:5 and 93:7 DCM

Sources & evidence

ORD record
ord-21fa1ae761f141d98886f27b3eba35db
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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