Triethylamine → (2-Bromopyridin-3-yl)methanol

HRID 1473903Notes

Reaction equation

HRID 1473903 reaction equation
[Br:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(N(CC)CC)C.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.O>[Br:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 2332622-Bromopyridine-3-carboxylic acidHCID 4311764Sodium borohydride

Product 1

HCID 14761460(2-Bromopyridin-3-yl)methanolYield 90.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-bromonicotinic acid (4.0 g, 20 mmol) and triethylamine (3.34 mL, 24 mmol, 1.2 eq.) in THF (100 mL) was added i-butyl chloroformate (3.12 mL, 24 mmol, 1.2 eq.) at 0° C. The mixture was stirred at 0° C. for 10 min and filtered. To this filtrate was added a suspension of NaBH4 (1.52 g, 40 mmol, 2 eq.) in water (1.0 mL) at 0° C. The mixture was stirred for 30 min, added water (3 mL), continued to stir for 2 h, and concentrated to dryness. The crude was purified on silica gel using a mixture of ethylacetate and hexanes as eluent to give (2-bromopyridin-3-yl)methanol (3.4 g, 90%) as a white solid. LRMS (M+H+) m/z 188.0.

Workup

  1. filtrationfiltered
  2. additionTo this filtrate was added
  3. stirringThe mixture was stirred for 30 min
  4. stirringto stir for 2 h
  5. concentrationconcentrated to dryness
  6. customThe crude was purified on silica gel using
  7. additiona mixture of ethylacetate and hexanes as eluent

Sources & evidence

ORD record
ord-f8cf047a6c194398bba655cb354ad5c3
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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