Dimethylformamide → [2-(6-Fluoropyridin-2-yl)-imidazol-1-yl]acetic acid tert-butyl ester

HRID 895532Notes

Reaction equation

HRID 895532 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)[N:3]=1.Br[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:18]([O:17][C:15](=[O:16])[CH2:14][N:9]1[CH:10]=[CH:11][N:12]=[C:8]1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[N:3]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 219192862-Fluoro-6-(1h-imidazol-2-yl)pyridine

Product 1

HCID 68495227[2-(6-Fluoropyridin-2-yl)-imidazol-1-yl]acetic acid tert-butyl esterYield 90.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-Fluoro-6-(1H-imidazol-2-yl)pyridine (410 mg; 2.51 mmol), tert-butyl bromoacetate (539 mg; 2.76 mmol), potassium carbonate (520 mg; 3.77 mmol), and N,N-dimethylformamide (20 mL) is stirred at room temperature for 16 h. Water (60 mL) is added and the mixture extracted with ethyl acetate (3×70 mL). The organic extracts are washed with water (3×40 mL) and brine (1×40 mL), dried (MgSO4), and concentrated to give [2-(6-Fluoropyridin-2-yl)-imidazol-1-yl]acetic acid tert-butyl ester as an orange oil (630 mg). 1H NMR (CDCl3) δ 8.12 (dd,1H), 7.82(q,1H), 7.16(s,1H), 6.98(s,1H), 6.81(dd,1H), 5.14(s,2H), 1.44s,(9H), LCMS: 276.1(M−).

Workup

  1. extractionthe mixture extracted with ethyl acetate (3×70 mL)
  2. washThe organic extracts are washed with water (3×40 mL) and brine (1×40 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9ef392038b5440aca3c20134c0d76b63
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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