4-Fluoroiodobenzene → Methyl 3-fluoro-1-(4-fluorophenyl)-1H-indole-6-carboxylate

HRID 403311

반응식

HRID 403311 반응식
[F:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:23][C:24]1[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=1.CNC1CCCCC1NC>[Cu]I.C1(C)C=CC=CC=1>[F:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[N:4]([C:27]2[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=2)[CH:3]=1

참가 물질

7

반응물 4

HCID 96054-FluoroiodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 59625843methyl 3-fluoro-1H-indole-6-carboxylate

생성물 1

HCID 59625701Methyl 3-fluoro-1-(4-fluorophenyl)-1H-indole-6-carboxylate

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 1140Toluene용매

반응 조건

온도
95 °C

실험 절차

Compound 21a (51 mg, 0.264 mmol), CuI (5 mg, 0.0264 mmol) and K3PO4 (40 mg, 0.66 mmol) were combined in a sealed reaction tube and the vial was back-flushed with N2. 4-Fluoro-iodobenzene 21b (0.0394 mL, 0.264 mmol) and N,N′-dimethylcyclohexane-1,2-diamine (0.0125 mL, 0.0792 mmol) were added via syringe, followed by toluene. The reaction mixture was heated at 95° C. for 6 h. The reaction was partitioned between EtOAc and water. The organic phase was concentrated and purified by flash column chromatography (silica gel, 20% EtOAc/hexanes) to give compound 21c.

후처리

  1. customthe vial was back-flushed with N2
  2. customThe reaction was partitioned between EtOAc and water
  3. concentrationThe organic phase was concentrated
  4. custompurified by flash column chromatography (silica gel, 20% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-398a1f72757d400f8076e6663bf66744
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748417B2

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