6-Bromo-N,N-dimethylnicotinamide → 4-(5-Dimethylcarbamoyl-pyridin-2-yloxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([O:16]C2C=NC(C(=O)N(C)C)=CC=2)[C:8]2[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[CH:6]=1)=[O:4].Br[C:29]1[CH:39]=[CH:38][C:32]([C:33]([N:35]([CH3:37])[CH3:36])=[O:34])=[CH:31][N:30]=1.COC(C1C=C(O)C2CC(C)(C)OC=2C=1)=O>>[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([O:16][C:29]2[CH:39]=[CH:38][C:32]([C:33](=[O:34])[N:35]([CH3:36])[CH3:37])=[CH:31][N:30]=2)[C:8]2[CH2:9][C:10]([CH3:12])([CH3:13])[O:11][C:7]=2[CH:6]=1)=[O:4]Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared in a similar manner as described for Intermediate 161b, from 6-bromo-N,N-dimethyl-nicotinamide (162a) (335 mg, 1.46 mmol) and 4-hydroxy-2,2-dimethyl-2,3-dihydrobenzofuran-6-carboxylic acid methyl ester (3e) (250 mg, 1.12 mmol) to give a white foam (200 mg, 50% yield). 1H NMR (400 MHz, CDCl3) δ 8.26 (d, J=2.02 Hz, 1 H) 7.83 (dd, J=8.46, 2.40 Hz, 1 H) 7.34 (d, J=1.01 Hz, 1 H) 7.27 (s, 1 H) 6.97 (d, J=8.34 Hz, 1 H) 3.86 (s, 3 H) 3.08 (d, J=21.47 Hz, 6 H) 2.82 (s, 2 H) 1.46 (s, 6 H); LCMS for C20H22N2O5 m/z 371.20 (M+H+).
Sources & evidence
- ORD record
- ord-c05e833e7bc741d2a1a0794a8b2b2f06
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842713B2
Reaction notes
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