Hydrochloric Acid → Methyl 4-(benzylthio)-2-(4-fluoroanilino)benzoate

HRID 2191687Notes

Reaction equation

C1(C)C=CC=CC=1.[F:8][C:9]1[CH:26]=[CH:25][C:12]([NH:13][C:14]2[CH:23]=[C:22](I)[CH:21]=[CH:20][C:15]=2[C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=1.[C:27]1([CH2:33][SH:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C.C(N(CC)CC)C>[CH2:33]([S:34][C:22]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([NH:13][C:12]2[CH:25]=[CH:26][C:9]([F:8])=[CH:10][CH:11]=2)[CH:23]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To toluene 4.0 mL suspension of methyl 2-(4-fluoroanilino)-4-iodobenzoate 0.40 g, 1,1′-bis(diphenylphosphino)ferrocene 0.072 g and tris(dibenzylideneacetone)dipalladium(0) 0.050 g were added triethylamine 0.30 mL and phenylmethanethiol 0.15 mL, and it was stirred under argon atmosphere at 80° C. for 2 hours. After the reaction mixture was cooled to room temperature, 1.0 mol/L hydrochloric acid and ethyl acetate were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent, hexane:ethyl acetate=10:1] to give methyl 4-(benzylthio)-2-(4-fluoroanilino)benzoate 0.36 g of white solid.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
customThe organic layer was separated
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-cb498fe1674b45dba75bcf21a79098a8
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08327467B2

Reaction notes

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