Sodium Carbonate → 1-(6-(3,6-Dihydro-2H-pyran-4-yl)pyridin-2-yl)-3-(8-fluoroquinolin-4-yl)urea

HRID 1528094노트

반응식

HRID 1528094 반응식
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[NH:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18](I)[N:17]=1)=[O:14].[O:23]1[CH2:28][CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH2:25][CH2:24]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:23]1[CH2:24][CH:25]=[C:26]([C:18]2[N:17]=[C:16]([NH:15][C:13]([NH:12][C:7]3[C:6]4[C:11](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=4)[N:10]=[CH:9][CH:8]=3)=[O:14])[CH:21]=[CH:20][CH:19]=2)[CH2:27][CH2:28]1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 866674931-(8-Fluoroquinolin-4-yl)-3-(6-iodopyridin-2-yl)urea

생성물 1

HCID 575212631-(6-(3,6-Dihydro-2H-pyran-4-yl)pyridin-2-yl)-3-(8-fluoroquinolin-4-yl)urea수율 23.6%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

1-(8-Fluoroquinolin-4-yl)-3-(6-iodopyridin-2-yl)urea (250 mg, 0.582 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (187 mg, 0.873 mmol), sodium carbonate solution (2M, 1.31 mL, 2.62 mmol) and tetrakis(triphenylphosphine)-palladium(0) (68 mg, 0.058 mmol) were dissolved in 5 ml of DMF under an argon atmosphere and the mixture was stirred at 80° C., in a microwave oven, for one hour. After the solvent had been evaporated down to dryness, the resulting residue was treated with water and the mixture was then extracted with ethyl acetate. After the combined organic phases had been dried over sodium sulfate and the solvent had been filtered and evaporated down to dryness, the resulting residue was purified by column chromatography to give the title product (50 mg, 19%).

후처리

  1. customAfter the solvent had been evaporated down to dryness
  2. additionthe resulting residue was treated with water
  3. extractionthe mixture was then extracted with ethyl acetate
  4. dry with materialAfter the combined organic phases had been dried over sodium sulfate
  5. filtrationthe solvent had been filtered
  6. customevaporated down to dryness
  7. customthe resulting residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-54f77c36cfe74601865aace10a9570f1
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090592B2

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