Ethanol → 4-(4-Chlorophenyl)-1-[3-(5,11-dihydro-7-ethoxycarbonyl-[1]benzoxepino[2,3-b]pyridin-5-ylidene) propyl]piperidine-4-ol

HRID 556937ノート

反応式

HRID 556937 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:40])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[O:21][C:20]4[CH:28]=[CH:29][CH:30]=[C:31](OS(C(F)(F)F)(=O)=O)[C:19]=4[CH2:18]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH2:77]([OH:79])[CH3:78].CN([CH:83]=[O:84])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:40])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]=[C:17]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[O:21][C:20]4[CH:28]=[CH:29][CH:30]=[C:31]([C:83]([O:79][CH2:77][CH3:78])=[O:84])[C:19]=4[CH2:18]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

参加物

7

反応物 5

HCID 702EthanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 734559704-(4-Chlorophenyl)-1-[3-(5,11-dihydro-7-trifluoromethanesulfonyloxy[1]benzoxepino[2,3-b]pyridin-5-ylidene)propyl]piperidin-4-ol

生成物 1

HCID 667586834-(4-Chlorophenyl)-1-[3-(5,11-dihydro-7-ethoxycarbonyl-[1]benzoxepino[2,3-b]pyridin-5-ylidene) propyl]piperidine-4-ol収率 73%

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

反応条件

温度
60 °C

実験手順

The compound of Example 169 (0.166 g) was dissolved in DMF (1 mL) and treated with palladium (II) acetate (0.007 g), 1,3-bis-diphenylphosphinopropane (0.012 g), triethylamine (0.1 mL) and ethanol (1 mL), and stirred at 60° C. for 18 hours under a CO balloon. The resulting solution was quenched with water, extracted with ethyl acetate, concentrated in vacuo, and purified by silica gel chromatography (87:10:3 ethyl acetate:methanol:triethylamine). The residue was further purified by chromatography on a reverse-phase solid-phase-extraction column, eluting with water-acetonitrile, 0.1% formic acid, to yield 0.114 g (73%) of the title compound.

後処理

  1. customThe resulting solution was quenched with water
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated in vacuo
  4. custompurified by silica gel chromatography (87:10:3 ethyl acetate:methanol:triethylamine)
  5. customThe residue was further purified by chromatography on a reverse-phase solid-phase-extraction column
  6. washeluting with water-acetonitrile, 0.1% formic acid

出典と根拠

ORDレコード
ord-4b8e4a41e57c4c22b37ef4cba85338e2
出典データセット
uspto-grants-2011_11
特許番号
US08058287B2

反応ノート

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