Methanol → HCID 178497324, compound

HRID 1067253Notes

Reaction equation

[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16](I)=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:31][OH:32].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN([CH:65]=[O:66])C>CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([C:31]([O:66][CH3:65])=[O:32])=[CH:15][CH:14]=3)=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-iodo-3-quinolinecarboxamide from Preparation No. 1 (30.0 g), Et3N (19.1 mL), MeOH (110.6 mL), Pd(OAc)2 (431 mg), and 1,3-bis (diphenylphosphino) propane (791.9 mg) in 375 mL anhydrous DMF is stirred at room temperature until everything dissolves. CO(g) is slowly bubbled through for 2 days and the reaction is maintained at 70° C. The reaction is cooled to room temperature. The product is precipitated by adding 160 ML 1N HCl to the reaction mixture. An orange solid precipitates and is collected. The solid is triturated with EtOAc, filtered, and washed with CH2Cl2 to afford 23.8 g (93%) of the title compound as an off-white solid.

Workup

dissolutiondissolves
customCO(g) is slowly bubbled through for 2 days
temperatureThe reaction is cooled to room temperature
customThe product is precipitated
additionby adding 160 ML 1N HCl to the reaction mixture
customAn orange solid precipitates
customis collected
customThe solid is triturated with EtOAc
filtrationfiltered
washwashed with CH2Cl2

Sources & evidence

ORD record: ord-84b9da5ca4614c34a2b935d81bf2e178
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248736B1

Reaction notes

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