5-Bromo-6-methoxypyridine-3-carbaldehyde → HCID 58539347, compound

HRID 554651Notes

Reaction equation

HRID 554651 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[O:11])[CH:5]=[N:6][C:7]=1[O:8][CH3:9].C(OC(=O)C1C=C(Br)C(OC)=NC=1)C.C([BH-](CC)CC)C.[Li+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][OH:11])[CH:5]=[N:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 123924165-Bromo-6-methoxypyridine-3-carbaldehydeHCID 23664628LithiumtriethylborohydrideHCID 463114835-Bromo-6-methoxy-nicotinic acid ethyl ester

Product 1

HCID 58539347HCID 58539347, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 5-bromo-6-methoxy-pyridine-3-carbaldehyde and 5-bromo-6-methoxy-nicotinic acid ethyl ester (3 g, 13.9 mmol) was dissolved in THF (30 mL) and cooled to 0° C., and lithium triethylborohydride (1M in THF; 42 mL, 42 mmol) was added. The reaction was stirred for 5 minutes, and then quenched with EtOH, acidified with 1N aqueous HCl, and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated to give (5-bromo-6-methoxy-pyridin-3-yl)-methanol.

Workup

  1. customquenched with EtOH
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f5369398a812423582f99d67acc272d0
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

Loading…