Potassium Carbonate → 3-(4-Amino-2-fluorophenyl)-5-bromopyridin-2-amine

HRID 1428097Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4](I)[C:5]([NH2:8])=[N:6][CH:7]=1.[F:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1B1OC(C)(C)C(C)(C)O1)[NH2:14].C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>O1CCOCC1.O.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>[NH2:14][C:13]1[CH:15]=[CH:16][C:17]([C:4]2[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)=[C:11]([F:10])[CH:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

5-Bromo-3-iodopyridin-2-amine (300 mg), 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (238 mg), tetrakis(triphenylphosphine)palladium (58 mg) and potassium carbonate (416 mg) were suspended in dioxane (5 ml) and water (0.5 ml), and the suspension was heated under reflux at 80° C. for two days. After leaving to cool, a saturated aqueous sodium bicarbonate solution was added, and the organic layer was extracted with ethyl acetate and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [hexane:ethyl acetate=1:2 (v/v)] to give 248 mg of the title compound as a solid.

Workup

customAfter leaving
temperatureto cool
extractionthe organic layer was extracted with ethyl acetate
dry with materialdried over sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe residue was purified by silica gel column chromatography [hexane:ethyl acetate=1:2 (v/v)]

Sources & evidence

ORD record: ord-9e855f16dac34369b4d194728a9c6b29
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933103B2

Reaction notes

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