Water → HCID 59774854, compound

HRID 2387275Notes

Reaction equation

HRID 2387275 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=2)[NH:13][CH:12]=1)[OH:10].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([O:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:18]=2)[NH:13][CH:12]=1)=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 59774812HCID 59774812, compound

Product 1

HCID 59774854HCID 59774854, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (2,4-dichloro-phenyl)-(5-phenoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (33, 48 mg, 0.12 mmol) in tetrahydrofuran (15 mL), Dess-Martin periodinane (58 mg, 0.137 mmol) was added. The reaction was stirred at room temperature for 40 minutes, then poured into water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtrated and concentrated. The crude material was suspended in acetonitrile (1˜2 mL). The precipitated material was collected with vacuum filtration to provide the compound (P-0036, 24 mg, 50%). MS (ESI) [M+H+]+=383.1 and 385.1.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium bicarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated
  6. filtrationThe precipitated material was collected with vacuum filtration
  7. customto provide the compound (P-0036, 24 mg, 50%)

Sources & evidence

ORD record
ord-50de641719cc414986cccde04d2b023b
Source dataset
uspto-grants-2012_09
Patent number
US08268858B2

Reaction notes

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