Triacetoxyperiodinane → (1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanone

HRID 2204642노트

반응식

HRID 2204642 반응식
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][CH:32]([CH:36]([C:38]2[C:43]([Cl:44])=[CH:42][N:41]=[C:40]3[N:45]([Si:48]([CH:55]([CH3:57])[CH3:56])([CH:52]([CH3:54])[CH3:53])[CH:49]([CH3:51])[CH3:50])[CH:46]=[CH:47][C:39]=23)[OH:37])[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[CH2:23]([N:30]1[CH2:35][CH2:34][CH2:33][CH:32]([C:36]([C:38]2[C:43]([Cl:44])=[CH:42][N:41]=[C:40]3[N:45]([Si:48]([CH:52]([CH3:54])[CH3:53])([CH:55]([CH3:57])[CH3:56])[CH:49]([CH3:50])[CH3:51])[CH:46]=[CH:47][C:39]=23)=[O:37])[CH2:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 58010130(1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanol

생성물 1

HCID 58010051(1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanone수율 25%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Dess-Martin periodinane (14.63 g, 34.5 mmol) was added to a solution of (1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanol (5.89 g, 11.5 mmol) in DCM (120 mL) at about 0° C. and the resulting mixture was stirred for about 16 h while warming to ambient temperature. The solvent was removed under reduced pressure and the residue partitioned between saturated aqueous NaHCO3 (150 mL) and EtOAc (200 mL). The organic phase was washed with brine (120 mL) and concentrated under reduced pressure. Purification by silica gel chromatography eluting first with heptane (1 L) and then with 1:7 EtOAc:heptane (1 L) yielded (1-benzylpiperidin-3-yl)(5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)methanone (1.45 g, 25%) as a yellow oil: LC/MS (Table 2, Method a) Rt=3.24 min; MS m/z: 511 (M+H)+

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between saturated aqueous NaHCO3 (150 mL) and EtOAc (200 mL)
  3. washThe organic phase was washed with brine (120 mL)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by silica gel chromatography
  6. washeluting first with heptane (1 L)

출처 및 근거

ORD 기록
ord-9cd1c09d5c104cbbbe6f2ba4546b6ff9
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365579B2

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