Potassium Phosphate, Tribasic → Ethyl 2-[6-{1-[(1,1-dimethylethyl)(dimethyl)silyl]-1H-indol-4-yl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate

HRID 2036058노트

반응식

HRID 2036058 반응식
Cl[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:4]([C:20]2[O:21][C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][N:24]=2)[CH:3]=1.[CH3:30][C:31]([Si:34]([CH3:48])([CH3:47])[N:35]1[C:43]2[C:38](=[C:39](B(O)O)[CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36]1)([CH3:33])[CH3:32].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.Cl[Pd]C1C=CC=CC=1C1C=CC=CC=1N(C)C.[C@H]12C[C@H](CC1)CC2PC1C[C@H]2C[C@@H]1CC2>[CH3:33][C:31]([Si:34]([CH3:48])([CH3:47])[N:35]1[C:43]2[C:38](=[C:39]([C:2]3[CH:10]=[C:9]4[C:5]([CH:6]=[N:7][N:8]4[S:11]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)(=[O:13])=[O:12])=[C:4]([C:20]4[O:21][C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][N:24]=4)[CH:3]=3)[CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36]1)([CH3:30])[CH3:32]

참가 물질

7

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 223523971-(tert-Butyldimethylsilyl)-1H-indole-4-boronic acidHCID 59564714HCID 59564714, 화합물

생성물 1

HCID 59564707Ethyl 2-[6-{1-[(1,1-dimethylethyl)(dimethyl)silyl]-1H-indol-4-yl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate수율 38.9%

시약·촉매·용매 3

HCID 178420574HCID 178420574, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

To a solution of ethyl 2-[6-chloro-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-oxazole-5-carboxylate (1.5 g, 3.47 mmol) in 1,4-dioxane (15 ml) and water (1.5 ml) was added {1-[(1,1-dimethylethyl)(dimethyl)silyl]-1H-indol-4-yl}boronic acid (1.243 g, 4.52 mmol, available from Combi-Blocks Inc.), chloro[2′-(dimethylamino)-2-biphenylyl]palladium-1(1R,4S)-bicyclo[2.2.1]hept-2-yl[(1S,4R)-bicyclo[2.2.1]hept-2-yl]phosphane (0.097 g, 0.174 mmol) and potassium phosphate tribasic (2.212 g, 10.42 mmol). The reaction mixture was heated to 100° C. for 3 h, the solvent removed in vacuo and the residue partitioned between dichloromethane (20 ml) and water (10 ml). Saturated sodium chloride solution (100 ml) was added and the organic phase separated and dried over anhydrous sodium sulphate. The crude product was purified by silica gel chromatography, eluting with a gradient of cyclohexane and ethyl acetate. The desired fractions were concentrated to give the title compound as a white solid (0.846 g), which by LCMS contained some unreacted starting material.

후처리

  1. customthe solvent removed in vacuo
  2. customthe residue partitioned between dichloromethane (20 ml) and water (10 ml)
  3. additionSaturated sodium chloride solution (100 ml) was added
  4. customthe organic phase separated
  5. dry with materialdried over anhydrous sodium sulphate
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of cyclohexane and ethyl acetate
  8. concentrationThe desired fractions were concentrated

출처 및 근거

ORD 기록
ord-7697c185c3954d0c87774dcfe3e81891
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575162B2

반응 노트

불러오는 중…