Sodium borohydride → 1-(1-(2-Bromoethyl)-3-(2,5-dimethyl-1H-pyrrol-1-yl)-1H-pyrazol-5-yl)ethanol

HRID 1185198Notes

Reaction equation

HRID 1185198 reaction equation
[Br:1][CH2:2][CH2:3][N:4]1[C:8]([C:9](=[O:11])[CH3:10])=[CH:7][C:6]([N:12]2[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]2[CH3:18])=[N:5]1.[BH4-].[Na+]>CO>[Br:1][CH2:2][CH2:3][N:4]1[C:8]([CH:9]([OH:11])[CH3:10])=[CH:7][C:6]([N:12]2[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]2[CH3:18])=[N:5]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866840481-(1-(2-Bromoethyl)-3-(2,5-dimethyl-1H-pyrrol-1-yl)-1H-pyrazol-5-yl)ethanone

Product 1

HCID 866840491-(1-(2-Bromoethyl)-3-(2,5-dimethyl-1H-pyrrol-1-yl)-1H-pyrazol-5-yl)ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 100-mL round-bottomed flask equipped with a magnetic stirrer was charged with 150e (2.1 g, 1.0 eq., 6.8 mmol), NaBH4 (1.29 g, 5.0 eq., 34.0 mmol), and methanol (50 mL). The mixture was stirred at room temperature for 2 h and quenched with water (30 mL). It was then concentrated under reduced pressure and the residue was extracted with dichloromethane (3×50 mL). The combined organic layer was concentrated under reduced pressure to afford crude 150f, which was used in the next step without further purification. MS-ESI: [M+H]+ 311.9

Workup

  1. customA 100-mL round-bottomed flask equipped with a magnetic stirrer
  2. customquenched with water (30 mL)
  3. concentrationIt was then concentrated under reduced pressure
  4. extractionthe residue was extracted with dichloromethane (3×50 mL)
  5. concentrationThe combined organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7f3c3d70b82949dea8c1dbfa08da8357
Source dataset
uspto-grants-2014_03
Patent number
US08669251B2

Reaction notes

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