Sodium Carbonate → HCID 67185001、化合物

HRID 1020021ノート

反応式

HRID 1020021 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1B(O)O.[CH2:13]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH2:26][CH:25]([C:29](=[O:38])[NH:30][C:31]2[CH:36]=[C:35](Cl)[N:34]=[CH:33][N:32]=2)[CH2:24]1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][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>[CH2:13]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH2:26][CH:25]([C:29](=[O:38])[NH:30][C:31]2[CH:36]=[C:35]([C:3]3[C:4]([O:8][CH3:9])=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[N:34]=[CH:33][N:32]=2)[CH2:24]1)=[O:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 3294524(2-Fluoro-6-methoxyphenyl)boronic acidHCID 86645892HCID 86645892、化合物

生成物 1

HCID 67185001HCID 67185001、化合物収率 71.8%

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 2-fluoro-6-methoxyphenyl boronic acid (0.20 g, 1.1 mmol) in a mixture of THF and water (6 ml, 1:1), 3-(6-chloro-pyrimidin-4-ylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester (0.35 g, 0.93 mmol) was added at 0° C. followed by palladium acetate (12 mg, 54 μmol), 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: 66.7%) of 3-[6-(2-fluoro-6-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-551eb81421fa4d78bd1175747fb94d37
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…