Benzyl Alcohol → HCID 117667757, compound

HRID 712710Notes

Reaction equation

HRID 712710 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[N:6][CH:7]=1.[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:12]([O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 28025392-(5-Bromopyridin-3-yl)acetic acid

Product 1

HCID 117667757HCID 117667757, compoundYield 42.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (5-bromo-pyridin-3-yl)-acetic acid (2.0 g, 9.3 mmol), benzyl alcohol (1.0 g, 9.2 mmol), DCC (1.9 g, mmol), and DMAP (1.0 g, mmol) in DCM (30 mL) is stirred at room temperature for 16 h. The mixture is filtered and the filtrate is concentrated to give the crude product. Purification by flash column chromatography affords 1.2 g of (5-bromo-pyridin-3-yl)-acetic acid benzyl ester.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. customto give the crude product
  4. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-4927835074f14db7b435cd519d7d3e96
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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