Triethylamine → (Z)-tert-butyl 5-(benzyloxy)-3-(3-morpholino-3-oxoprop-1-enyl)-1H-indole-1-carboxylate

HRID 573064

反応式

HRID 573064 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:13]=[C:12]2Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:26]1[CH2:31][CH2:30][N:29]([C:32](=[O:35])[CH:33]=[CH2:34])[CH2:28][CH2:27]1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.[Cl-].[NH4+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:13]=[C:12]2/[CH:34]=[CH:33]\[C:32]([N:29]1[CH2:30][CH2:31][O:26][CH2:27][CH2:28]1)=[O:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

9

反応物 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 98723AcryloylmorpholineHCID 404285545-(Benzyloxy)-3-bromo-1H-indole, N-BOC protected

生成物 1

HCID 67227351(Z)-tert-butyl 5-(benzyloxy)-3-(3-morpholino-3-oxoprop-1-enyl)-1H-indole-1-carboxylate

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
100 °C

実験手順

A mixture of tert-butyl 5-(benzyloxy)-3-bromo-1H-indole-1-carboxylate (2.011 g), 1-morpholinoprop-2-en-1-one (0.776 g), palladium acetate (31 mg), tri-o-tolylphosphine (187 mg) and triethylamine (1.14 mL) in N,N-dimethylformamide (14 mL) under nitrogen atmosphere was stirred at 100° C. overnight. The mixture was diluted with ethyl acetate and saturated ammonium chloride. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (80% ethyl acetate-hexane) to give the desired product.

後処理

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. dry with materialthe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (80% ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-73b57b0cfd00485b8716c6d5aa974531
出典データセット
uspto-grants-2015_05
特許番号
US09029404B2

関連ノート

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