Potassium Acetate → 5-(5,7-Difluoro-3-methyl-2-(4-methylpyridin-2-yl)quinolin-4-ylamino)pyridin-3-ylboronic acid

HRID 1431601Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([F:20])=[CH:16][C:17]=3[F:19])[N:12]=[C:11]([C:21]3[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][N:22]=3)[C:10]=2[CH3:28])[CH:5]=[N:6][CH:7]=1.[B:29]1(B2OC(C)(C)C(C)(C)O2)[O:33]C(C)(C)C(C)(C)[O:30]1.C([O-])(=O)C.[K+]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.O1CCOCC1>[F:19][C:17]1[CH:16]=[C:15]([F:20])[CH:14]=[C:13]2[C:18]=1[C:9]([NH:8][C:4]1[CH:3]=[C:2]([B:29]([OH:33])[OH:30])[CH:7]=[N:6][CH:5]=1)=[C:10]([CH3:28])[C:11]([C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][N:22]=1)=[N:12]2

Participants

Conditions

Temperature: 95 °C

Procedure

A screwcap vial was charged with N-(5-bromopyridin-3-yl)-5,7-difluoro-3-methyl-2-(4-methylpyridin-2-yl)quinolin-4-amine (225 mg, 0.510 mmol), bis(pinacolato)diboron (194 mg, 0.77 mmol), bis(triphenylphosphine)palladium (II) chloride (35.8 mg, 0.051 mmol), potassium acetate (100 mg, 1.02 mmol), and 1,4-dioxane (5 mL). The mixture was stirred at 95° C. under nitrogen for 18 h, and cooled to rt. The desired product was extracted with DCM and EtOAc, and the combined organic layer was dried over magnesium sulfate and cond. This afforded crude 5-(5,7-difluoro-3-methyl-2-(4-methylpyridin-2-yl)quinolin-4-ylamino)pyridin-3-ylboronic acid. Mass Spectrum (ESI) m/e=407.1 (M+1).

Workup

temperaturecooled to rt
extractionThe desired product was extracted with DCM and EtOAc
dry with materialthe combined organic layer was dried over magnesium sulfate and cond

Sources & evidence

ORD record: ord-489343e745da4ddabb462c48739abe40
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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