Isopropanol → 6-(1H-Indol-4-yl)-1-methyl-4-nitro-1H-indazole

HRID 1615977노트

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HRID 1615977 반응식
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH3:11])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.[NH:15]1[C:23]2[C:18](=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16]1.CC(O)C.C(=O)(O)[O-].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(OCC)(=O)C>[NH:15]1[C:23]2[C:18](=[C:19]([C:2]3[CH:10]=[C:9]4[C:5]([CH:6]=[N:7][N:8]4[CH3:11])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=3)[CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16]1

참가 물질

7

반응물 4

HCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 27631731H-Indole-4-boronic acidHCID 58267997HCID 58267997, 화합물

생성물 1

HCID 582679906-(1H-Indol-4-yl)-1-methyl-4-nitro-1H-indazole수율 43%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 8857Ethyl Acetate용매

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온도
150 °C

실험 절차

6-Bromo-1-methyl-4-nitro-1H-indazole (100 mg, 0.39 mmol), Pd(dppf)Cl2 (32 mg, 0.04 mmol) and 1H-indol-4-ylboronic acid (94 mg, 0.59 mmol) were treated with a 4:1 mixture of propan-2-ol and saturated sodium bicarbonate solution (3 ml) and the reaction was heated in a microwave at 150° C. for 10 mins. Ethyl acetate was added, a solid was filtered off and the filtrate was partitioned between ethyl acetate and water. The water was washed twice with ethyl acetate and the combined organics were washed with brine, dried over magnesium sulphate, filtered and evaporated. The residue was purified by silica chromatography, eluting with 0-25% ethyl acetate in cyclohexane. Appropriate fractions were combined and evaporated to give the title compound (49 mg) as an orange solid.

후처리

  1. filtrationa solid was filtered off
  2. customthe filtrate was partitioned between ethyl acetate and water
  3. washThe water was washed twice with ethyl acetate
  4. washthe combined organics were washed with brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by silica chromatography
  9. washeluting with 0-25% ethyl acetate in cyclohexane
  10. customevaporated

출처 및 근거

ORD 기록
ord-5a8cf03d7b0e4feab10b1f4540082b41
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765743B2

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