Reaction equation
F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(C(C)C)CC)(C)C.[NH:34]1[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([C:43]([OH:45])=O)[CH:41]=2)[CH:36]=[CH:35]1.[CH3:46][O:47][C:48](=[O:57])[C:49]1[CH:54]=[CH:53][C:52]([NH2:55])=[CH:51][C:50]=1[Cl:56]>O1CCCC1>[CH3:46][O:47][C:48](=[O:57])[C:49]1[CH:54]=[CH:53][C:52]([NH:55][C:43]([C:40]2[CH:41]=[C:42]3[C:37]([CH:36]=[CH:35][NH:34]3)=[CH:38][CH:39]=2)=[O:45])=[CH:51][C:50]=1[Cl:56]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (8.3 g, 17.8 mmol, 1.1 equiv.) and diisopropyl ethyl amine (4.4 ml, 33.9 mmol, 2.1 equiv.) were added to 1H-indole-6-carboxylic acid (2.6 g, 16.2 mmol, 1 equiv.) in tetrahydrofuran (30 mL) and the mixture was shaken for 5 minutes at room temperature. 4-Amino-2-chlorobenzoic acid methyl ester (3.3 g, 17.9 mmol, 1.1 equiv.) was added and the resultant mixture was shaken at room temperature for 16 hours. The solvent was removed under vacuum and the residue triturated with dichloromethane (10 mL). The solid was filtered to afford 2-chloro-4-[(1H-indole-6-carbonyl)-amino]-benzoic acid methyl ester, 1.4 g (26% yield). LC @215 nm; Rt 1.36: 90%, m/z (ES+): 329 (M+H+.); δH (400 MHz; d6-DMSO) 11.65 (1H, s), 10.59 (1H, s), 8.16 (1H, s), 8.10 (1H, s), 7.93 (2H, m), 7.65 (2H, s), 7.59 (1H, m), 6.62 (1H, s), 3.85 (3H, s).
Workup
- customThe solvent was removed under vacuum
- customthe residue triturated with dichloromethane (10 mL)
- filtrationThe solid was filtered
Sources & evidence
- ORD record
- ord-f6120e17224a4b6085e2cad556988c9b
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07713996B2
Linked notes
Loading…