Water → HCID 60133233, 화합물

HRID 2246619노트

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HRID 2246619 반응식
I[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.[CH2:11]([NH:13][C:14](=[O:31])[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17](B2OC(C)(C)C(C)(C)O2)[CH:16]=1)[CH3:12].C(=O)([O-])O.[Na+].O>C(O)(C)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:11]([NH:13][C:14](=[O:31])[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[N:7][NH:8]3)=[CH:4][CH:3]=2)[CH:16]=1)[CH3:12]

참가 물질

7

반응물 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 129912416-iodo-1H-indazoleHCID 60133236HCID 60133236, 화합물2회

생성물 1

HCID 60133233HCID 60133233, 화합물수율 48.5%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 3776Isopropanol용매

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온도
150 °C

실험 절차

A stirred mixture of 6-iodo-1H-indazole (0.45 g), N-ethyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Intermediate 10, 0.54 g) tetrakis(triphenylphosphine)palladium(0) (0.05 g) and aqueous sodium hydrogen carbonate (1M, 1 ml) in isopropanol (10 ml) was heated at 150° C. for 30 min in a microwave oven. The reaction mixture was poured into water (50 ml) and extracted with ethyl acetate (3×25 ml). The extracts were washed with water (25 ml) dried (Na2SO4) and concentrated under vacuum. The residual oil was purified by column chromatography on silica (50 g) eluting with ether/ethyl acetate (7:3) to give the title compound as a pale yellow foam (0.25 g).

후처리

  1. extractionextracted with ethyl acetate (3×25 ml)
  2. washThe extracts were washed with water (25 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under vacuum
  5. customThe residual oil was purified by column chromatography on silica (50 g)
  6. washeluting with ether/ethyl acetate (7:3)

출처 및 근거

ORD 기록
ord-8ce90d8d807246a2ba95ce223afebe35
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687532B2

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