Potassium Phosphate, Tribasic → (E)-ethyl 3-(5-chloropent-1-enyl)-5-fluoro-1-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate

HRID 533278ノート

反応式

HRID 533278 の反応式
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([F:11])[CH:9]=2)[N:4]([CH2:12][CH2:13][CH2:14][O:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[C:3]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27].[Cl:31][CH2:32][CH2:33][CH2:34]/[CH:35]=[CH:36]/B1OC(C)(C)C(C)(C)O1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(O[Pd]OC(=O)C)(=O)C>[Cl:31][CH2:32][CH2:33][CH2:34]/[CH:35]=[CH:36]/[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([F:11])[CH:9]=2)[N:4]([CH2:12][CH2:13][CH2:14][O:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)[C:3]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

参加物

6

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 111281322-[(1E)-5-Chloro-1-penten-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 67316184ethyl 3-bromo-5-fluoro-1-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate

生成物 1

HCID 86630290(E)-ethyl 3-(5-chloropent-1-enyl)-5-fluoro-1-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

反応条件

温度
100 °C

実験手順

A mixture of ethyl 3-bromo-5-fluoro-1-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate (The synthesis of this compound was described in EXAMPLE 134B as an intermediate) (404 mg), (E)-2-(5-chloropent-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.394 ml), diacetoxypalladium (19.28 mg), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (70.5 mg) and K3PO4 (547 mg) was heated in a microwave reactor (CEM Discover) at 100° C. for 1 hour. The insoluble material was removed by filtration and the filtrate was concentrated. The residue was purified by flash chromatography, eluting with dichloromethane to provide the title compound.

後処理

  1. customThe synthesis of this compound
  2. customThe insoluble material was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by flash chromatography
  5. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-7ebb30a835e04004a1aa260f62bb0acc
出典データセット
uspto-grants-2014_10
特許番号
US08853209B2

反応ノート

読み込み中…