m-Chloroperbenzoic acid → HCID 66743545, compound

HRID 1259348Notes

Reaction equation

HRID 1259348 reaction equation
[OH:1][CH:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[C:4](=[O:11])[N:3]1[C:12]1[CH:13]=[N:14][N:15]([CH2:17][C:18]([F:21])([F:20])[F:19])[CH:16]=1.C1C=C(Cl)C=C(C(OO)=[O:30])C=1>C(Cl)(Cl)Cl.CO>[OH:1][CH:2]1[C:6]2=[N+:7]([O-:30])[CH:8]=[CH:9][CH:10]=[C:5]2[C:4](=[O:11])[N:3]1[C:12]1[CH:13]=[N:14][N:15]([CH2:17][C:18]([F:21])([F:20])[F:19])[CH:16]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 66743220HCID 66743220, compound2×

Product 1

HCID 66743545HCID 66743545, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

As shown in step 18-i of Scheme 18, to 7-hydroxy-6-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (Compound 2055, 4.35 g, 14.6 mmol) in CHCl3 (80 mL) and MeOH (40 mL) was added mCPBA (5.39 g, 21.9 mmol). After stirring for 24 hours, additional mCPBA (1.26 g, 7.30 mmol) was added. After stirring an additional 16 hours, the resulting precipitate was collected by filtration and washed with DCM (10 mL) and Et2O (20 mL) to give 7-hydroxy-5-oxo-6-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine 1-oxide (Compound 2059, 2.49 g) as a white solid: ESMS (M+H) 315.25; 1H NMR (DMSO-d6, 300 MHz) δ 8.44 (d, J=6 Hz, 1H), 8.31 (s, 1H), 7.89 (s, 1H), 7.65 (m, 2H), 7.43 (d, J=9 Hz, 1H), 6.41 (d, J=9 Hz, 1H), 5.20 (q, J=9 Hz, 2H).

Workup

  1. stirringAfter stirring an additional 16 hours
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with DCM (10 mL) and Et2O (20 mL)

Sources & evidence

ORD record
ord-7422d9592432436e918372464c51cc3a
Source dataset
uspto-grants-2013_06
Patent number
US08466288B2

Reaction notes

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