3-Methyl-2-furoic acid → N-(3-ethynylphenyl)-3-methylfuran-2-carboxamide
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])#[CH:2].[CH3:10][C:11]1[CH:15]=[CH:14][O:13][C:12]=1[C:16](O)=[O:17].C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O>[C:1]([C:3]1[CH:4]=[C:5]([NH:6][C:16]([C:12]2[O:13][CH:14]=[CH:15][C:11]=2[CH3:10])=[O:17])[CH:7]=[CH:8][CH:9]=1)#[CH:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To the solution of 3-ethynylaniline (1.2 mL, 11.2 mmol, 1.0 eq) in anhydrous DMF (25 mL) was added 3-methyl-furan-2-carboxylic acid (1.84 g, 1.3 eq), diisopropylethyl amine (7.85 mL, 4.0 eq), and BOP (6.72 g, 1.35 eq). After the reaction solution was heated at 60° C. for two hours, it was cooled to room temperature, diluted with EtOAc, washed sequentially with aqueous NH4Cl, water, brine, and lastly dried with anhydrous sodium sulfate. The clear solution was decanted, concentrated, and the yellow oily residue was subject to column chromatography (EtOAc-Hex from 1:100 to 1:10). The product eluting fractions were concentrated to give the title compound as a yellow oil.
Workup
- temperatureit was cooled to room temperature
- washwashed sequentially with aqueous NH4Cl, water, brine
- dry with materiallastly dried with anhydrous sodium sulfate
- customThe clear solution was decanted
- concentrationconcentrated
- washThe product eluting fractions
- concentrationwere concentrated
Sources & evidence
- ORD record
- ord-edd39b7c41734954babcf29bab288513
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266869B2
Reaction notes
Loading…