HCID 59272956, 화합물 → HCID 135910367, 화합물

HRID 2423106노트

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HRID 2423106 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:26]C)=[C:6]2[C:10]=1[N:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17]CC3C=CC=CC=3)=[C:13]([F:25])[CH:12]=1)[N:8]=[CH:7]2>Br>[F:1][C:2]1[C:10]2[N:9]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:25])[CH:12]=3)[N:8]=[CH:7][C:6]=2[C:5]([OH:26])=[CH:4][CH:3]=1

참가 물질

3

반응물 1

HCID 59272956HCID 59272956, 화합물

생성물 1

HCID 135910367HCID 135910367, 화합물수율 23%

시약·촉매·용매 1

HCID 260Hydrogen Bromide용매

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온도
120 °C

실험 절차

7-Fluoro-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-(methyloxy)-1H-indazole (D27) (280 mg, 0.764 mmol) was dissolved in HBr (48% aq., 15 mL) and refluxed at 120° C. under argon. After 2 hours the mixture was partitioned between DCM (50 mL)/water (50 mL), the pH adjusted to 7 by addition of a 2M solution of NaOH and the layers separated. The aqueous phase was extracted with DCM (3×50 mL) and the combined organics were washed with brine (50 mL), separated and dried over MgSO4, filtered and concentrated in vacuo. The crude material (198 mg) was purified by flash chromatography (Biotage SP4) with a gradient of 0-100% Et2O in hexane. The isolated material (75 mg) was further purified by MDAP to afford 46 mg of the title compound (E13).

후처리

  1. customAfter 2 hours the mixture was partitioned between DCM (50 mL)/water (50 mL)
  2. additionthe pH adjusted to 7 by addition of a 2M solution of NaOH
  3. customthe layers separated
  4. extractionThe aqueous phase was extracted with DCM (3×50 mL)
  5. washthe combined organics were washed with brine (50 mL)
  6. customseparated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude material (198 mg) was purified by flash chromatography (Biotage SP4) with a gradient of 0-100% Et2O in hexane
  11. customThe isolated material (75 mg) was further purified by MDAP

출처 및 근거

ORD 기록
ord-93244fbac6b84eb1b7d15dceedc46e36
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960563B2

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