Potassium Carbonate → 6-Fluoro-1-[1-[6-(1-methylpyrazol-4-yl)pyridazin-3-yl]piperidin-4-yl]-2,3-dihydroindole

HRID 512822노트

반응식

HRID 512822 반응식
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([F:23])[CH:21]=4)[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:24][N:25]1[CH:29]=[C:28](B2OC(C)(C)C(C)(C)O2)[CH:27]=[N:26]1.C([O-])([O-])=O.[K+].[K+]>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>[F:23][C:20]1[CH:21]=[C:22]2[C:17]([CH2:16][CH2:15][N:14]2[CH:11]2[CH2:12][CH2:13][N:8]([C:5]3[N:6]=[N:7][C:2]([C:28]4[CH:27]=[N:26][N:25]([CH3:24])[CH:29]=4)=[CH:3][CH:4]=3)[CH2:9][CH2:10]2)=[CH:18][CH:19]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 896144661-(1-(6-Chloropyridazin-3-yl)piperidin-4-yl)-6-fluoroindoline

생성물 1

HCID 715715696-Fluoro-1-[1-[6-(1-methylpyrazol-4-yl)pyridazin-3-yl]piperidin-4-yl]-2,3-dihydroindole

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

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온도
100 °C

실험 절차

In a two-neck flask was placed 1-(1-(6-chloropyridazin-3-yl)piperidin-4-yl)-6-fluoroindoline, prepared as in STEP 3 above (2.33 g, 7 mmol, 1 equiv), 1-methylpyrazole-4-boronic acid pinacol ester (1.75 g, 8.4 mmol, 1.2 equiv), K2CO3 (3.86 g, 28 mmol, 4.0 equiv), and Pd(PPh3)4 (809 mg, 0.7 mmol, 0.1 equiv). The resulting mixture was degassed and refilled with N2 (3 times). 1,4-Dioxane/H2O (30 mL/6 mL) was added and the resulting mixture was heated at 100° C. for 3 h. The resulting mixture was poured into EtOAc/H2O (100 mL/100 mL). The organic layer was washed with brine (100 mL), dried (Na2SO4), and filtered. The solvent was removed by roto-evaporator, and the resulting residue was purified by column using EtOAc as the eluent to yield the title compound as a solid.

후처리

  1. customIn a two-neck flask was placed
  2. customThe resulting mixture was degassed
  3. additionrefilled with N2 (3 times)
  4. addition1,4-Dioxane/H2O (30 mL/6 mL) was added
  5. additionThe resulting mixture was poured into EtOAc/H2O (100 mL/100 mL)
  6. washThe organic layer was washed with brine (100 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customThe solvent was removed by roto-evaporator
  10. customthe resulting residue was purified by column

출처 및 근거

ORD 기록
ord-a85c23ff2eb54f1a9b9d4b86646b8c57
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102669B2

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