Potassium Acetate → 5-(5,7-Difluoro-3-methyl-2-(4-methylpyridin-2-yl)quinolin-4-ylamino)pyridin-3-ylboronic acid
반응식
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]2참가 물질
6
반응물 3
생성물 1
시약·촉매·용매 2
반응 조건
- 온도
- 95 °C
실험 절차
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).
후처리
- 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
출처 및 근거
- ORD 기록
- ord-489343e745da4ddabb462c48739abe40
- 출처 데이터셋
- uspto-grants-2015_01
- 특허 번호
- US08940724B2
반응 노트
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