Potassium Carbonate → 5-Chloro-2-methyl-[3,5'-bi-1-indole]-1-acetic acid, ethyl ester

HRID 418456

반응식

HRID 418456 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]([CH3:15])=[C:5]2[C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1N=CC=C2.[NH:26]1C2C(=CC(B(O)O)=CC=2)[CH:28]=[CH:27]1.C(=O)([O-])[O-].[K+].[K+].[C:44]1(C)C=CC=C[C:45]=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([O:14][CH2:44][CH3:45])=[O:13])[CH:6]([CH3:15])[C:5]2=[C:16]1[CH:17]=[CH:18][C:19]2[C:20]([CH:28]=[CH:27][N:26]=2)=[CH:25]1

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 27343615-Indolylboronic acidHCID 103832715-Chloro-2-methyl-3-(8-quinolinyl)-1H-indole-1-acetic acid

생성물 1

HCID 867614855-Chloro-2-methyl-[3,5'-bi-1-indole]-1-acetic acid, ethyl ester

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 180Acetone용매HCID 962Water용매

실험 절차

The product of Example 51 part b (200 mg), 5-indole boronic acid (100 mg), potassium carbonate (0.73 g), acetone (6 ml), water (3 ml), palladium acetate (12 mg) and tri(o-tolyl) phosphine (30 mg) were heated at 90° C. for 4 hours. The reaction mixture was concentrated in vacuo, purified by silica chromatography eluting with hexane:EtOAc (7:3) to give the sub-title compound (140 mg).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by silica chromatography
  3. washeluting with hexane:EtOAc (7:3)

출처 및 근거

ORD 기록
ord-30f7720dcc3e4848865d428ed4cda11c
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093278B2

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