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

HRID 1013320노트

반응식

HRID 1013320 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3d596d18c387462ebd55d6d4c591787c
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981888B2

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