Lithium borohydride → HCID 10138256, compound

HRID 2422985Notes

Reaction equation

HRID 2422985 reaction equation
C([O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][N:11]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]4=[O:27])=[CH:17][CH:16]=3)[C:10](=[O:28])[C:9]=2[N:8]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[N:7]=1)=O)C.[Li+].[BH4-]>C1COCC1>[OH:3][CH2:4][C:6]1[C:14]2[CH2:13][CH2:12][N:11]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]4=[O:27])=[CH:17][CH:16]=3)[C:10](=[O:28])[C:9]=2[N:8]([C:29]2[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)[N:7]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 10277738HCID 10277738, compound

Product 1

HCID 10138256HCID 10138256, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 1-(4-methoxy-phenyl)-7-oxo-6-[4-(2-oxo-2H-pyridin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (0.2 g, 0.4 mmol) in THF (25 mL) was added 2M LiBH4 in THF (0.31 mL, 0.66 mmol) and the reaction was heated to reflux for 3 h. After extraction into EtOAc and washing with water and brine, the product crystallized out upon standing; High Resolution Mass Spec (M+H)+ for C25H23N4O4 443.1730.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 3 h
  3. extractionAfter extraction into EtOAc
  4. washwashing with water and brine
  5. customthe product crystallized out

Sources & evidence

ORD record
ord-f9a1de66cbf8460f81a633a16544cb41
Source dataset
uspto-grants-2011_06
Patent number
US07960411B2

Reaction notes

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