Sodium Carbonate → 2-(2-Fluoro-6-methoxyphenyl)-8-methylquinoline-3-carbaldehyde

HRID 216766

반응식

HRID 216766 반응식
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:17]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>CC#N.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>[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:17]=1[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 6890822-Chloro-8-methylquinoline-3-carboxaldehydeHCID 3294524(2-Fluoro-6-methoxyphenyl)boronic acid

생성물 1

HCID 577078192-(2-Fluoro-6-methoxyphenyl)-8-methylquinoline-3-carbaldehyde

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

Prepared according to Procedure A using 2-chloro-8-methylquinoline-3-carbaldehyde (1.07 g, 5.21 mmol), 2-fluoro-6-methoxyphenylboronic acid (0.9738 g, 5.73 mmol, 1.1 eq), tetrakis(triphenylphosphine)palladium (0.3011 g, 5% mmol), and sodium carbonate (2.76 g, 26.1 mol, 5 eq) in MeCN (37.5 mL) and water (12.5 mL). After purification, 2-(2-fluoro-6-methoxyphenyl)-8-methylquinoline-3-carbaldehyde was obtained as white solid. 1H NMR (DMSO-d6) δ ppm 9.88 (1H, s), 8.95 (1H, s), 8.10 (1H, d, J=8.1 Hz), 7.82 (1H, d, J=7.1 Hz), 7.62-7.69 (1H, m), 7.49-7.59 (1H, m), 6.96-7.10 (2H, m), 3.71 (3H, s), 2.70 (3H, s). Mass Spectrum (ESI) m/e=296.0 (M+1).

후처리

  1. customPrepared
  2. customAfter purification

출처 및 근거

ORD 기록
ord-c7c82070863c4b699c4f6c2c2557213a
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193199B2

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