Triethylamine → 4-[(1E)-3-tert-butoxy-3-oxoprop-1-enyl]-2-{[(5-methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}benzoic acid

HRID 1182240Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([NH:12][C:13](=[O:27])[CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH3:25])[CH:22]=3)[NH:17][C:16]=2[CH3:26])[CH:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:50]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])(=[O:53])[CH:51]=[CH2:52].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[C:55]([O:54][C:50](=[O:53])/[CH:51]=[CH:52]/[C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:12][C:13](=[O:27])[CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH3:25])[CH:22]=3)[NH:17][C:16]=2[CH3:26])[CH:3]=1)([CH3:58])([CH3:57])[CH3:56]

Participants

Conditions

Temperature: 110 °C

Procedure

To methyl 4-bromo-2-{[(5-methoxy-2-methyl-1H-indol-3-yl)acetyl]amino}benzoate (20 mg) was added palladium acetate (2 mg), tri-o-tolylphosphine (3 mg), t-butyl acrylate (33 μl), triethylamine (32 μl) and dimethylformamide (1 ml). After heating at 110° C. for 18 h, the solvent was removed in vacuo and the residue diluted with dichloromethane (10 ml) and washed with 5% citric acid (5 ml). Purification by SPE eluting with dichloromethane, chloroform, and chloroform: ether mixtures afforded the title compound (5 mg), MH+ 465; MH− 463; TR 4.47 min.

Workup

customthe solvent was removed in vacuo
additionthe residue diluted with dichloromethane (10 ml)
washwashed with 5% citric acid (5 ml)
customPurification by SPE
washeluting with dichloromethane, chloroform, and chloroform

Sources & evidence

ORD record: ord-b2bc124e14cd41968e00321aeb615b81
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288564B2

Reaction notes

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