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 60102ノート

反応式

HRID 60102 の反応式
[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]

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-478ac231d31f45eba141dc915f7d3d96
出典データセット
uspto-grants-2016_09
特許番号
US09440969B2

反応ノート

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