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2-Methyl-2-butene → 6-fluoro-5-[4-(1-hydroxycyclobutyl)-3-methoxyphenyl]-1H-indole-3-carboxylic acid

HRID 1054633
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HRID 1054633 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=O)=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2([OH:23])[CH2:22]O[CH2:20]2)=[C:15]([O:24][CH3:25])[CH:14]=1.[CH3:26]C(=CC)C.Cl([O-])=O.[Na+].[OH2:35].[OH2:36].P([O-])(O)(O)=O.[Na+]>CC#N.O.C(O)(C)(C)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:36])=[O:35])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2([OH:23])[CH2:20][CH2:26][CH2:22]2)=[C:15]([O:24][CH3:25])[CH:14]=1
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참가 물질

8

반응물 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 866986366-fluoro-5-[4-(3-hydroxyoxetan-3-yl)-3-methoxyphenyl]-1H-indole-3-carbaldehyde

생성물 1

HCID 866986386-fluoro-5-[4-(1-hydroxycyclobutyl)-3-methoxyphenyl]-1H-indole-3-carboxylic acid수율 8.1%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 6386tert-Butanol용매

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온도
0 °C

실험 절차

6-fluoro-5-[4-(3-hydroxyoxetan-3-yl)-3-methoxyphenyl]-1H-indole-3-carbaldehyde (86 mg, 0.2534 mmol) was dissolved in MeCN (6 mL) and warm t-butanol (6 mL). 2-methyl-2-butene (4 mL) was then added and cooled to 0° C. Sodium chlorite (342 mg, 5.07 mmol) and sodium dihydrogen phosphate dihydrate (791 mg, 5.07 mmol) were dissolved in water (3 mL). The aqueous solution was added to the organic solution dropwise via addition funnel and the ice bath was removed and the mixture was allowed to warm to room temperature. The reaction was quenched with saturated aqueous sodium sulfite, concentrated to remove the organics and extracted with EtOAc (20 mL×3). The combined organics were washed with brine (20 mL), dried and concentrated to give a crude residue, which was purified by prep HPLC to afford the title compound (7.3 mg, 8.1%) as an off-white solid.

후처리

  1. additionThe aqueous solution was added to the organic solution dropwise via addition funnel
  2. customthe ice bath was removed
  3. temperatureto warm to room temperature
  4. customThe reaction was quenched with saturated aqueous sodium sulfite
  5. concentrationconcentrated
  6. customto remove the organics and
  7. extractionextracted with EtOAc (20 mL×3)
  8. washThe combined organics were washed with brine (20 mL)
  9. customdried
  10. concentrationconcentrated
  11. customto give a crude residue, which
  12. customwas purified by prep HPLC

출처 및 근거

ORD 기록
ord-100137f02b664cf3948297fe58ecbf13
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09394285B2

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