Potassium Phosphate, Tribasic → 1-Ethyl-3-[7-(2-fluoro-phenyl)-5-pyridin-3-yl-benzothiazol-2-yl]-urea

HRID 447017노트

반응식

HRID 447017 반응식
Br[C:2]1[C:10]2[S:9][C:8]([NH:11][C:12]([NH:14][CH2:15][CH3:16])=[O:13])=[N:7][C:6]=2[CH:5]=[C:4]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:3]=1.[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.CO>[CH2:15]([NH:14][C:12]([NH:11][C:8]1[S:9][C:10]2[C:2]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[F:23])=[CH:3][C:4]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:5][C:6]=2[N:7]=1)=[O:13])[CH3:16]

참가 물질

6

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 27343542-Fluorophenylboronic acidHCID 248642171-(7-Bromo-5-pyridin-3-yl-benzothiazol-2-yl)-3-ethyl-urea

생성물 1

HCID 578136721-Ethyl-3-[7-(2-fluoro-phenyl)-5-pyridin-3-yl-benzothiazol-2-yl]-urea수율 23%

시약·촉매·용매 2

HCID 887Methanol용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

A stirred mixture of 1-(7-Bromo-5-pyridin-3-yl-benzothiazol-2-yl)-3-ethyl-urea (50 mg, 0.133 mmol), 2-fluorobenzeneboronic acid (19 mg, 0.139 mmol), powdered potassium phosphate tribasic (34 mg, 0.160 mmol) and 1,1′-bis(diphenylphosphino)ferrocene palladium(II)chloride complex (16 mg, 0.01995 mmol) in anhydrous 1,4-dioxane (1 ml) and anhydrous methanol (2 ml) was purged with nitrogen for 5 min and heated in a sealed vessel for 16 h at 80° C. After cooling to ambient temperature, the mixture was filtered through kieselguhr. The kieselguhr was thoroughly washed with methanol and the combined filtrates evaporated to dryness in vacuo to give the crude 1-Ethyl-3-[7-(2-fluoro-phenyl)-5-pyridin-3-yl-benzothiazol-2-yl]-urea which was purified by “flash” silica chromatography eluting with 0 to 30% methanol in ethyl acetate. 12 mg of a pale-brown solid was obtained.

후처리

  1. customwas purged with nitrogen for 5 min
  2. temperatureAfter cooling to ambient temperature
  3. filtrationthe mixture was filtered through kieselguhr
  4. washThe kieselguhr was thoroughly washed with methanol
  5. customthe combined filtrates evaporated to dryness in vacuo
  6. customto give the crude 1-Ethyl-3-[7-(2-fluoro-phenyl)-5-pyridin-3-yl-benzothiazol-2-yl]-urea which
  7. customwas purified by “flash” silica chromatography
  8. washeluting with 0 to 30% methanol in ethyl acetate

출처 및 근거

ORD 기록
ord-0e5c461ea39945338199a313585a7c76
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481544B2

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