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Triacetoxyperiodinane → (6-ethoxy-pyridin-3-yl)-[6-fluoro-5-(5-methyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

HRID 1396168
Notes
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Reaction equation

HRID 1396168 reaction equation
[C:1]([O:5][C:6](=[O:46])[N:7]([C:37]1[CH:38]=[N:39][C:40]([O:43][CH2:44][CH3:45])=[CH:41][CH:42]=1)[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:35])[C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([CH3:24])[CH:22]=3)[N:17]([Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[CH:16]=2)=[C:10]([F:36])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]([O:5][C:6](=[O:46])[N:7]([C:37]1[CH:38]=[N:39][C:40]([O:43][CH2:44][CH3:45])=[CH:41][CH:42]=1)[C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([CH3:24])[CH:22]=3)[N:17]([Si:25]([CH:29]([CH3:30])[CH3:31])([CH:32]([CH3:33])[CH3:34])[CH:26]([CH3:28])[CH3:27])[CH:16]=2)=[O:35])=[C:10]([F:36])[N:9]=1)([CH3:2])([CH3:4])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58485882(6-Ethoxy-pyridin-3-yl)-{6-fluoro-5-[hydroxy-(5-methyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-pyridin-2-yl}-carbamic acid tert-butyl ester

Product 1

HCID 58485918(6-ethoxy-pyridin-3-yl)-[6-fluoro-5-(5-methyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-pyridin-2-yl]-carbamic acid tert-butyl esterYield 50.1%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

(6-Ethoxy-pyridin-3-yl)-{6-fluoro-5-[hydroxy-(5-methyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-pyridin-2-yl}-carbamic acid tert-butyl ester (70, 0.400 g, 0.616 mmol) is alternatively dissolved in 11.8 mL of dichloromethane, and Dess-Martin periodinane (0.100 g, 0.236 mmol) is added. The reaction is stirred at room temperature for 30 minutes, then concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with 20-100% ethyl acetate in hexane. Appropriate fraction are combined and concentrated under vacuum to provide the desired compound (71, 0.200 g).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe resulting material is purified by silica gel column chromatography
  3. washeluting with 20-100% ethyl acetate in hexane
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c505a78b74b945b788158e47de977853
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08901118B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes