Sodium Carbonate → HCID 67183854、化合物

HRID 1020020ノート

反応式

HRID 1020020 の反応式
[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

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27826735-Fluoro-2-methoxyphenylboronic acidHCID 86645892HCID 86645892、化合物

生成物 1

HCID 67183854HCID 67183854、化合物収率 66.7%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-fe7bd06d63354163b74e16e5b509033c
出典データセット
uspto-grants-2014_05
特許番号
US08716296B2

反応ノート

読み込み中…