Sodium borohydride → 1-(1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazol-3-yl)ethanol

HRID 885065Notes

Reaction equation

HRID 885065 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([N:9]2[CH:13]=[N:12][C:11]([C:14](=[O:16])[CH3:15])=[N:10]2)=[C:5]2[NH:17][CH:18]=[CH:19][C:4]=12.[BH4-].[Na+]>CO.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3]1[CH:8]=[N:7][C:6]([N:9]2[CH:13]=[N:12][C:11]([CH:14]([OH:16])[CH3:15])=[N:10]2)=[C:5]2[NH:17][CH:18]=[CH:19][C:4]=12

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 580260551-(1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazol-3-yl)ethanone

Product 1

HCID 580260541-(1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazol-3-yl)ethanolYield 57.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1-(1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazol-3-yl)ethanone (50 mg, 0.194 mmol) in MeOH (3 mL) was added sodium borohydride (14.71 mg, 0.389 mmol) at 0° C. After stirring at room temperature for 3 h, the reaction was diluted with 5% NaHCO3 (5 mL) and extracted with EtOAc (2×30 mL). The organic layers were combined and concentrated. The residue was purified by prep. HPLC to give 1-(1-(4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl)-1H-1,2,4-triazol-3-yl)ethanol (29 mg, 0.112 mmol, 57.5% yield). LCMS: m/z 260.2 (M+H)+, 1.47 min (method 8). 1H NMR (500 MHz, MeOD) δ ppm 9.17 (s, 1H) 7.51 (s, 1H) 7.45 (d, J=3.05 Hz, 1H) 6.67 (d, J=3.05 Hz, 1H) 5.09 (q, J=6.51 Hz, 1H) 4.02 (s, 3H) 1.63 (d, J=6.41 Hz, 3H).

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. concentrationconcentrated
  3. customThe residue was purified by prep

Sources & evidence

ORD record
ord-2dae74bc0da84953b0045aca2fcc2bd9
Source dataset
uspto-grants-2012_08
Patent number
US08242124B2

Reaction notes

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