Sodium Carbonate → 7-Fluoro-8-methyl-2-(5-methylpyridin-3-yl)quinoline-3-carbaldehyde

HRID 572132노트

반응식

HRID 572132 반응식
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:15])[C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=1.[CH3:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[N:21][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+]>O.COCCOC.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:14][C:6]1[C:5]([CH3:15])=[C:4]2[C:9]([CH:10]=[C:11]([CH:12]=[O:13])[C:2]([C:19]3[CH:20]=[N:21][CH:22]=[C:17]([CH3:16])[CH:18]=3)=[N:3]2)=[CH:8][CH:7]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 27627085-Methylpyridine-3-boronic acidHCID 866626352-Chloro-7-fluoro-8-methylquinoline-3-carbaldehyde

생성물 1

HCID 867011737-Fluoro-8-methyl-2-(5-methylpyridin-3-yl)quinoline-3-carbaldehyde수율 80%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

Prepared according to the procedure described for Intermediate 41, utilising 2-chloro-7-fluoro-8-methylquinoline-3-carbaldehyde (5.0 g, 22.36 mmol), 5-methylpyridin-3-ylboronic acid (6.95 g, 50.75 mmol), tetrakis(triphenylphosphine)palladium(0) (258 mg, 0.22 mmol) and Na2CO3 (3.55 g, 33.54 mmol) in water (30 mL) and DME (60 mL). The crude material was triturated in diethyl ether (75 mL), and the solid was filtered off and dried under vacuum to give the title compound (5.0 g, 80%) as a brown solid. δH (DMSO-d6) 10.12 (s, 1H), 9.06 (s, 1H), 8.72 (d, J 1.9 Hz, 1H), 8.60 (d, J 1.5 Hz, 1H), 8.24 (dd, J 9.0, 6.4 Hz, 1H), 7.99 (d, J 0.6 Hz, 1H), 7.68 (t, J 9.2 Hz, 1H), 2.66 (d, J 2.4 Hz, 3H), 2.44 (s, 3H). LCMS (ES+) 281 (M+H)+, RT 1.66 minutes.

후처리

  1. customPrepared
  2. customThe crude material was triturated in diethyl ether (75 mL)
  3. filtrationthe solid was filtered off
  4. customdried under vacuum

출처 및 근거

ORD 기록
ord-6a2f2307d890428f838b821384acbc70
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029392B2

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