Triethylamine → 3-methyl-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole

HRID 79250노트

반응식

HRID 79250 반응식
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=2)[N:3]=1.[C:22]1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C[Sn](C)(C)C.C(N(CC)CC)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN(C)C=O>[CH3:22][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=2)[N:3]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 11661TetramethyltinHCID 80271Tri-o-tolylphosphineHCID 672597623-iodo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole

생성물 1

HCID 672592993-methyl-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole수율 394.5%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

A dry, 100 mL round bottom flask equipped with a reflux condenser and a nitrogen line was charged with 3-iodo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole (Example 142, Step B; 100 mg, 0.254 mmol), tri-o-tolylphosphine (15.4 mg, 0.051 mmol), and tris(dibenzylideneacetone)dipalladium (0) (23 mg, 0.025 mmol). The flask was purged with nitrogen and anhydrous N,N-dimethylformamide (30 mL), and tetramethylstannane (0.04 mL, 0.28 mmol) were added, followed by triethylamine (0.04 mL, 0.30 mmol). The flask was thoroughly degassed under nitrogen and heated at 80° C. for 6 hours. The reaction mixture was cooled to ambient temperature, diluted with water, and extracted multiple times with DCM and EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was subjected to preparative thin-layer chromatography on silica with 2% MeOH-DCM as eluent to afford 56.8 mg of desired product as a yellow solid.

후처리

  1. customA dry, 100 mL round bottom flask equipped with a reflux condenser
  2. additionwere added
  3. customThe flask was thoroughly degassed under nitrogen
  4. temperatureThe reaction mixture was cooled to ambient temperature
  5. additiondiluted with water
  6. extractionextracted multiple times with DCM and EtOAc
  7. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-58f84488c8b348979457d82c21d3471b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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