HCID 66743584, compound → HCID 66743220, compound

HRID 1259346Notes

Reaction equation

HRID 1259346 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][N:4]1[CH:8]=[C:7]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[CH:6]=[N:5]1>CC(O)=O.[Zn]>[OH:19][CH:10]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:16]2[C:17](=[O:18])[N:9]1[C:7]1[CH:6]=[N:5][N:4]([CH2:3][C:2]([F:21])([F:20])[F:1])[CH:8]=1

Participants

4

Reactant 1

HCID 66743584HCID 66743584, compound2×

Product 1

HCID 66743220HCID 66743220, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
23 °C

Procedure

As shown in step 17-i of Scheme 17, to 6-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione (Compound 2048, 2.32 g, 7.832 mmol) in AcOH (30 mL) at 23° C. was added Zn (2.561 g, 39.16 mmol). After stirring for 20 minutes at 23° C., the reaction mixture was filtered through a glass frit, and the filtrate was concentrated. The residue was dissolved/suspended in hot EtOH (40 mL). The resulting mixture was cooled, treated with Et2O (50 mL). The resulting precipitate was collected by filtration and the mother liquor was concentrated under reduced pressure and the resulting solid recrystallized from hot EtOH (20 mL) and Et2O to give additional 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, 1.61 g total) as a yellow solid: ESMS (M+H) 299.26; 1H NMR (DMSO-d6, 300 MHz) δ 8.83 (dd, J=3, 6 Hz, 1H), 8.32 (s, 1H), 8.15 (dd, J=3, 9 Hz, 1H), 7.94 (s, 1H), 7.61 (dd, J=6, 9 Hz, 1H), 7.13 (d, J=9 Hz, 1H), 6.21 (d, J=9 Hz, 1H), 5.20 (q, J=9 Hz, 2H).

Workup

  1. filtrationthe reaction mixture was filtered through a glass frit
  2. concentrationthe filtrate was concentrated
  3. temperatureThe resulting mixture was cooled
  4. additiontreated with Et2O (50 mL)
  5. filtrationThe resulting precipitate was collected by filtration
  6. concentrationthe mother liquor was concentrated under reduced pressure
  7. customthe resulting solid recrystallized from hot EtOH (20 mL) and Et2O

Sources & evidence

ORD record
ord-c2cddcd353a04d318a9c5c8c882e622c
Source dataset
uspto-grants-2013_06
Patent number
US08466288B2

Reaction notes

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