Water → HCID 58086168, compound

HRID 1098427Notes

Reaction equation

HRID 1098427 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-762eb542f36e4378a0ed390126398414
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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