({3-Bromo-5-cyano-2-[(trifluoroacetyl)amino]phenyl}methyl)(triphenyl)phosphonium bromide → HCID 58138925, compound

HRID 2061565Notes

Reaction equation

[Br-].[Br:2][C:3]1[C:4]([NH:31][C:32](=O)[C:33]([F:36])([F:35])[F:34])=[C:5]([CH2:11][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=[C:7]([C:9]#[N:10])[CH:8]=1>CN(C=O)C>[CH3:8][CH2:3][CH2:4][CH:5]([CH3:11])[CH3:6].[F:34][C:33]([F:36])([F:35])[C:32]1[NH:31][C:4]2[C:5]([CH:11]=1)=[CH:6][C:7]([C:9]#[N:10])=[CH:8][C:3]=2[Br:2]

Participants

Conditions

Temperature: 130 °C

Procedure

({3-bromo-5-cyano-2-[(trifluoroacetyl)amino]phenyl}methyl)(triphenyl)phosphonium bromide (37.2 g, crude) was dissolved in DMF (150 mL) and the reaction mixture was heated to 130° C. stirring for 3 hrs. The reaction mixture was allowed to cool to room temperature then quenched with water (400 mL). The reaction mixture was then extracted with ethyl acetate (3×300 mL). The organic extract was washed with a 1:1 mixture of water:brine (2×600 mL), dried (MgSO4), filtered and the solvent was removed. The resulting residues were then purified by filtration through a pad of silica gel eluting with 2-10% EtOAc: isoHexane to give the title compound as an off-white solid (6 g);

Workup

temperatureto cool to room temperature
customthen quenched with water (400 mL)
extractionThe reaction mixture was then extracted with ethyl acetate (3×300 mL)
extractionThe organic extract
washwas washed with a 1:1 mixture of water
dry with materialbrine (2×600 mL), dried (MgSO4)
filtrationfiltered
customthe solvent was removed
filtrationThe resulting residues were then purified by filtration through a pad of silica gel eluting with 2-10% EtOAc

Sources & evidence

ORD record: ord-7f7d816a05964bc3846d156e39c71d2c
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283365B2

Reaction notes

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