4-Fluoro-2-methylaniline → HCID 57708076, compound

HRID 659711

Reaction equation

Cl[C:2]1[C:3]2[CH:12]=[N:11][N:10]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[F:20])[C:4]=2[N:5]([CH3:9])[C:6](=[O:8])[CH:7]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[F:55][C:56]1[CH:62]=[CH:61][C:59]([NH2:60])=[C:58]([CH3:63])[CH:57]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([F:19])[C:13]=1[N:10]1[C:4]2[N:5]([CH3:9])[C:6](=[O:8])[CH:7]=[C:2]([NH:60][C:59]3[CH:61]=[CH:62][C:56]([F:55])=[CH:57][C:58]=3[CH3:63])[C:3]=2[CH:12]=[N:11]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-chloro-1-(2,6-difluorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (36 mg, 0.1 mmol), tris(dibenzylideneacetone)dipalladium (0) (6 mg, 0.006 mmol), X-Phos (6 mg) and 4-fluoro-2-methylaniline (3 mg, 0.2 mmol) in toluene (3 mL) was treated with sodium t-butoxide (40 mg, 0.4 mmol), and heated to 100° C. for 18 h. After the mixture was cooled to RT, it was evaporated to dryness with some silica gel, and purified by silica gel chromatography to provide the title compound as an off-white crystalline solid. MS (ESI, pos.ion) m/z: 385.1 (M+1).

Workup

temperatureAfter the mixture was cooled to RT
customit was evaporated to dryness with some silica gel
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-5bc5bf218a6642cf97fded15955dc0d4
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080546B2

Linked notes

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