Water → HCID 58086168, compound

HRID 1261064Notes

Reaction equation

HRID 1261064 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[OH:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.O>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 68669139HCID 68669139, compound

Product 1

HCID 58086168HCID 58086168, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (3-nitro-phenyl)-(5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (P-1399, R═H, 500 mg, 1.44 mmol) in dimethylformamide (26 mL) was added Dess-Martin periodane (674 mg, 1.59 mmol). The reaction was stirred for one hour and the reaction was poured into water. All solids were filtered and purified by silica gel column chromatography eluting with 3% methanol in dichloromethane to give the compound (536, 295 mg, 59%). MS (ESI)[M+H+]+=345.2.

Workup

  1. filtrationAll solids were filtered
  2. custompurified by silica gel column chromatography
  3. washeluting with 3% methanol in dichloromethane
  4. customto give the compound (536, 295 mg, 59%)

Sources & evidence

ORD record
ord-e166d0dd87dc49099fc82a63d996ac66
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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