Tetrahydrofuran → propane-1-sulfonic acid (2,4-difluoro-3-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl)-amide

HRID 60102노트

반응식

HRID 60102 반응식
[F:1][C:2]1[C:7]([CH:8]([OH:27])[C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([B:18]4[O:22][C:21]([CH3:24])([CH3:23])[C:20]([CH3:26])([CH3:25])[O:19]4)[CH:16]=3)[NH:11][CH:10]=2)=[C:6]([F:28])[CH:5]=[CH:4][C:3]=1[NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31].O1CCCC1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[F:1][C:2]1[C:7]([C:8]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([B:18]4[O:19][C:20]([CH3:25])([CH3:26])[C:21]([CH3:23])([CH3:24])[O:22]4)[CH:16]=3)[NH:11][CH:10]=2)=[O:27])=[C:6]([F:28])[CH:5]=[CH:4][C:3]=1[NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:31])=[O:32]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 58368760propane-1-sulfonic acid (2,4-difluoro-3-{hydroxy-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-methyl}-phenyl)-amide

생성물 1

HCID 58368878propane-1-sulfonic acid (2,4-difluoro-3-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl)-amide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a reaction flask, propane-1-sulfonic acid (2,4-difluoro-3-{hydroxy-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-methyl}-phenyl)-amide (29, 0.155 g, 0.306 mmol) is combined with 10 mL of tetrahydrofuran and 3 mL of dichloromethane. Dess-Martin periodinane (0.648 g, 1.53 mmol) is added and the reaction is stirred at room temperature for 20 minutes. The reaction is mixed with 1N sodium thiosulfate, extracted with ethyl acetate and the organic layer dried and purified by silica gel column chromatography, eluting with a gradient of 20-100% ethyl acetate in hexanes. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound. MS (ESI) [M+H+]+=506.29.

후처리

  1. extractionextracted with ethyl acetate
  2. customthe organic layer dried
  3. custompurified by silica gel column chromatography
  4. washeluting with a gradient of 20-100% ethyl acetate in hexanes
  5. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-478ac231d31f45eba141dc915f7d3d96
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440969B2

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