Water → HCID 46909735, 화합물

HRID 1091906노트

반응식

HRID 1091906 반응식
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:9][CH:10]=[C:11]([CH:12]([OH:35])[C:13]3[C:14]([F:34])=[C:15]([NH:20][S:21]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)(=[O:23])=[O:22])[CH:16]=[CH:17][C:18]=3[F:19])[C:4]=12)#[CH:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O>O1CCCC1>[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:9][CH:10]=[C:11]([C:12]([C:13]3[C:14]([F:34])=[C:15]([NH:20][S:21]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)(=[O:22])=[O:23])[CH:16]=[CH:17][C:18]=3[F:19])=[O:35])[C:4]=12)#[CH:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 59487255HCID 59487255, 화합물

생성물 1

HCID 46909735HCID 46909735, 화합물수율 83.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To N-{3-[(4-ethynyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-2,4-difluoro-phenyl}-4-trifluoromethyl-benzenesulfonamide (8, 0.146 g, 0.288 mmol) dissolved in 15 mL of tetrahydrofuran, Dess-Martin periodinane (0.122 g, 0.288 mmol) was added. The reaction mixture was stirred at room temperature for 15 minutes. The reaction mixture was poured into water, extracted with ethyl acetate, and the organic layer separated and washed with brine, then dried over magnesium sulfate and filtered. The filtrate was concentrated under vacuum and the resulting material was purified by silica gel column chromatography, eluting with 0 to 30% ethyl acetate and hexane. The appropriate fractions were combined and the solvent removed under vacuum, and this material was further purified by silica gel column chromatography, eluting with 0 to 15% ethyl acetate and hexane. The appropriate fractions were combined and the solvent removed under vacuum to provide the desired compound (P-0001, 121 mg). MS (ESI) [M+H+]+=506.

후처리

  1. extractionextracted with ethyl acetate
  2. customthe organic layer separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under vacuum
  7. customthe resulting material was purified by silica gel column chromatography
  8. washeluting with 0 to 30% ethyl acetate and hexane
  9. customthe solvent removed under vacuum
  10. customthis material was further purified by silica gel column chromatography
  11. washeluting with 0 to 15% ethyl acetate and hexane
  12. customthe solvent removed under vacuum

출처 및 근거

ORD 기록
ord-e9c09e781e37423399f98f2bb9562331
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129404B2

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