Methyl 5-bromothiophene-2-carboxylate → Methyl 5-(3-aminopropyl)thiophene-2-carboxylate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10]#[C:11][CH2:12][NH:13]C(OC(C)(C)C)=O)=[CH:8][CH:9]=1)=[O:4].C(OC(=O)NCC#C)(C)(C)C.COC(C1SC(Br)=CC=1)=O>C(#N)C.CCOC(C)=O.C(N(CC)CC)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][NH2:13])=[CH:8][CH:9]=1)=[O:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
5-(3-tert-Butoxycarbonylamino-prop-1 ynyl)-thiophene-2-carboxylic acid methyl ester, A mixture of prop-2-ynyl-carbamic acid tert-butyl ester (1.67 g, 0.011 mmol), 5-bromo-thiophene-2-carboxylic acid methyl ester (2.50 g, 0.011 mmol), tetrakistriphenylphosphine(0) palladium (0.622 g, 0.0538 mmol), Cul (0.102 g, 0.538 mmol) and triethylamine (1.57 mL, 0.011 mmol) in 50 mL acetonitrile under nitrogen was heated at reflux for 16 h. The reaction was cooled to room temperature, diluted with 75 mL EtOAc, washed with 5.5% HCl, water and brine, dried over MgSO4, filtered and concentrated in vacuo to an oil. The product was purified via flash chromatography (9:1 to 4:1 hexanes:EtOAc) to afford the title compound as an oil (2.06 g). MS 313 (M+18).
Workup
- temperaturewas heated
- temperatureat reflux for 16 h
- washwashed with 5.5% HCl, water and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo to an oil
- customThe product was purified via flash chromatography (9:1 to 4:1 hexanes:EtOAc)
Sources & evidence
- ORD record
- ord-d6ca6eaf85ec442692e96c0b10ee928c
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06288120B1
Reaction notes
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