Methanol → HCID 178497324, compound

HRID 2290014Notes

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 Example No. 40 (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-64e98d691da5421687e66aff45fe66fd
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093732

Reaction notes

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