Water → 6-(1H-Indol-4-yl)-1-[(4-methylphenyl)sulfonyl]-1H-indazole-4-carbonitrile

HRID 38836노트

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HRID 38836 반응식
Br[C:2]1[CH:3]=[C:4]([C:21]#[N:22])[C:5]2[CH:6]=[N:7][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:9]=2[CH:10]=1.CC1(C)C(C)(C)OB([C:31]2[CH:39]=[CH:38][CH:37]=[C:36]3[C:32]=2[CH:33]=[CH:34][NH:35]3)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[NH:35]1[C:36]2[C:32](=[C:31]([C:2]3[CH:3]=[C:4]([C:21]#[N:22])[C:5]4[CH:6]=[N:7][N:8]([S:11]([C:14]5[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=5)(=[O:12])=[O:13])[C:9]=4[CH:10]=3)[CH:39]=[CH:38][CH:37]=2)[CH:33]=[CH:34]1

참가 물질

7

반응물 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 113224711H-Indole-4-boronic acid, pinacol esterHCID 666914596-bromo-1-(4-methylbenzenesulfonyl)-1H-indazole-4-carbonitrile

생성물 1

HCID 667767806-(1H-Indol-4-yl)-1-[(4-methylphenyl)sulfonyl]-1H-indazole-4-carbonitrile

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

To a suspension of 6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazole-4-carbonitrile in 1,4-dioxane (100 ml) was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (4.79 g, 10.72 mmol, available from Frontier Scientific Europe), 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride (2.061 g, 2.82 mmol) and potassium phosphate tribasic (8.97 g, 42.3 mmol). Water (20 ml) was added and the reaction mixture heated to 80° C. for 1 h. The solvent was removed and the residue partitioned between water (50 ml) and ethyl acetate (100 ml). The layers were filtered and the filtrate partitioned and concentrated, then purified by column chromatography, on a silica cartridge (300 g), eluting with a gradient of cyclohexane and ethyl acetate to give the title compound as a pale yellow solid (2.5 g).

후처리

  1. customThe solvent was removed
  2. customthe residue partitioned between water (50 ml) and ethyl acetate (100 ml)
  3. filtrationThe layers were filtered
  4. customthe filtrate partitioned
  5. concentrationconcentrated
  6. custompurified by column chromatography, on a silica cartridge (300 g)
  7. washeluting with a gradient of cyclohexane and ethyl acetate

출처 및 근거

ORD 기록
ord-9bbfb8de5abb4243aa37866019e44316
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524751B2

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