(5-Bromo-3-pyridinyl)methanol → HCID 68537937, compound

HRID 2267023Notes

Reaction equation

HRID 2267023 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1.[CH3:10][O:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([SH:19])[CH:14]=1>ClCCl.CO>[NH3:6].[CH3:10][O:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19][C:2]2[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][OH:9])[CH:3]=2)[CH:14]=1

Participants

5

Reactant 2

HCID 2784733(5-Bromo-3-pyridinyl)methanolHCID 4362804Methyl 3-mercaptobenzoate

Product 2

HCID 222AmmoniaYield 10%HCID 68537937HCID 68537937, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent2×

Procedure

Dissolve 3-bromo-5-hydroxymethyl-pyridinium chloridei [Kelly, T. R., Howard, H. R., Koe, K., Sarges, R. J. Med. Chem. 1985, 28, 1368-1371] (1.00 g, 4.45 mmol) in saturated aqueous sodium bicarbonate, extract three times with ethyl acetate, dry combined organic phases over sodium sulfate, condense to afford (5-bromo-pyridin-3-yl)-methanol. Employing the procedure of general method 1 using (5-bromo-pyridin-3-yl)-methanol (832 mg) and 3-mercapto-benzoic acid methyl ester (1.50 g, 8.91 mmol). Purify by SCX column, elute with dichloromethane, then 1:1 dichloromethane/methanol then 1:1 dichloromethane/methanol, 10% ammonia, compound elutes in the ammonia, to yield the title compound as a dark brown oil (380 mg, 1.38 mmol): MS (m/z): 276 (M+1).

Workup

  1. customPurify by SCX column
  2. washelute with dichloromethane

Sources & evidence

ORD record
ord-93faf1ca0a294e9f8636e4bebd4c10b8
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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