Water → HCID 58781075, compound

HRID 1161787Notes

Reaction equation

[I-].C[C:3]1[N:4](CC=C)[C:5]2[C:12]([F:13])=[C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=3[F:22])[C:10]([C:23]([O:25][CH3:26])=[O:24])=[CH:9][C:6]=2[N+:7]=1[CH3:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1CCCC1.O>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:13][C:12]1[C:5]2[N:4]=[CH:3][N:7]([CH3:8])[C:6]=2[CH:9]=[C:10]([C:23]([O:25][CH3:26])=[O:24])[C:11]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=1[F:22]

Participants

Conditions

Temperature: -10 °C

Procedure

A mixture of methyl 3-allyl-4-fluoro-5-(2-fluoro-4-iodophenylamino)-6-methoxycarbony-1-methyl-3H-benzoimidazol-1-ium iodide, triphenyl phosphine (0.62 g, 2.5 mmoles), palladium tetrakis (0.47 g, 0.48 mmoles) in dichloromethane (15 ml) is cooled at −10° C. Pyrrolidine (0.65 ml) is added dropwise and the reaction mixture is stirred for 2 hours. Water is added and the mixture is extracted with dichloromethane. The organic phases are combined, washed with brine, dried Na2SO4 and concentrated under reduced pressure. The resulting solid is triturated with a mixture of Hexane/Ether (9/1) and isolated by filtration.

Workup

extractionthe mixture is extracted with dichloromethane
washwashed with brine, dried Na2SO4
concentrationconcentrated under reduced pressure
customThe resulting solid is triturated with a mixture of Hexane/Ether (9/1)
customisolated by filtration

Sources & evidence

ORD record: ord-18e3fb5f01154f9da67c78c76cdb6292
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820664B2

Reaction notes

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