Sodium Carbonate → HCID 67183854, 화합물

HRID 1020020노트

반응식

HRID 1020020 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6](B(O)O)[CH:7]=1.Cl[C:14]1[N:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:30])[CH2:24]2)=[O:22])[CH:15]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:32]([O:31][C:29]([N:25]1[CH2:26][CH2:27][CH2:28][CH:23]([C:21](=[O:22])[NH:20][C:16]2[CH:15]=[C:14]([C:6]3[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[O:11][CH3:12])[N:19]=[CH:18][N:17]=2)[CH2:24]1)=[O:30])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 86645892HCID 86645892, 화합물

생성물 1

HCID 67183854HCID 67183854, 화합물수율 66.7%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-fluoro-2-methoxyphenyl boronic acid (0.20 g, 1.1 mmol) in a mixture of THF and water (6 ml, 1:1), benzyl 3-(6-chloropyrimidin-4-ylcarbamoyl)piperidine-1-carboxylate (0.35 g, 1.0 mmol) was added at 0° C. followed by palladium acetate (12 mg, 0.054 mmol), PPh3 (31 mg, 0.12 mmol) and saturated solution of sodium carbonate (2 ml). The reaction mixture was stirred at room temperature for 30 h and then filtered through a celite bed which was washed with ethyl acetate. The aqueous layer was extracted with ethyl acetate, the organic layers were combined, washed with brine, dried and evaporated under reduced pressure. The crude product was purified by column chromatography, using hexane/ethyl acetate (4:1) as eluent, to provide 0.31 g (yield: 53.8%) of 3-[6-(5-fluoro-2-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester

후처리

  1. additionwas added at 0° C.
  2. filtrationfiltered through a celite bed which
  3. washwas washed with ethyl acetate
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwashed with brine
  6. customdried
  7. customevaporated under reduced pressure
  8. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-fe7bd06d63354163b74e16e5b509033c
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716296B2

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