Water → HCID 58781075, compound

HRID 558190Notes

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-bbf0da5ac5d54fc395a44fb76ae52c5e
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063049B2

Reaction notes

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