Methyl 3-(bromomethyl)thiophene-2-carboxylate → Methyl 3-(aminomethyl)thiophene-2-carboxylate
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
Product 1
Reagents, catalysts & solvents 1
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
- concentrationconcentrated in vacuo
- customPurification of the residue by silica gel column chromatography
- washeluting with 95:5 and 93:7 DCM
Sources & evidence
- ORD record
- ord-2731d204b4554682ba663ce29377cda8
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893058B2
Reaction notes
Loading…