Ammonium Chloride → HCID 86700075, compound

HRID 1428122Notes

Reaction equation

I[C:2]1[C:3]([NH2:10])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9].CC1(C)C(C)(C)OB([C:19]2[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=2)O1.[F-].[Cs+].[Cl-].[NH4+]>CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[NH2:23][C:22]1[CH:24]=[CH:25][C:19]([C:2]2[C:3]([NH2:10])=[N:4][CH:5]=[CH:6][C:7]=2[O:8][CH3:9])=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3-Iodo-4-methoxypyridin-2-amine (350 mg), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (322 mg), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride-dichloromethane adduct (81 mg) and cesium fluoride (580 mg) were suspended in methanol (5.0 ml), and the suspension was heated under reflux at 80° C. for 19 hours. After leaving to cool, a saturated aqueous ammonium chloride 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 [ethyl acetate:dichloromethane:methanol=5:5:1 (v/v)] to give 245 mg of the title compound as a solid.

Workup

temperaturethe suspension was heated
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 [ethyl acetate:dichloromethane:methanol=5:5:1 (v/v)]

Sources & evidence

ORD record: ord-8c244f861e66497b9fc123d87b1078ba
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933103B2

Reaction notes

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