N-bromobutanimide → Ethyl 1-(5-bromo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxylate

HRID 710934

Reaction equation

HRID 710934 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[N:19]=[C:12]3[C:13]([O:17][CH3:18])=[CH:14][CH:15]=[CH:16][N:11]3[N:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Br:20]N1C(=O)CCC1=O>C(#N)C.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[N:19]=[C:12]3[C:13]([O:17][CH3:18])=[CH:14][CH:15]=[C:16]([Br:20])[N:11]3[N:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 580746401-(8-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 89651597Ethyl 1-(5-bromo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxylateYield 77%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridine-2-yl)-cyclopropanecarboxylic acid ethyl ester (25 g, 95.7 mmol) in acetonitrile (300 mL) at RT, N-bromosuccinimide (34 g, 191.5 mmol) was added portion wise. After addition the reaction mixture was stirred at RT for 6 hours. The reaction mixture was diluted with EtOAc (600 mL), washed with water (100 mL×2), brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated. The crude was purified by silica gel column chromatography (0 to 10% EtOAc in dichloromethane as eluent) to afford the title compound (25 g, 77%, colorless solid). 1H NMR (400 MHz, DMSO): δ=7.44 (d, J=8.4 Hz; 1H), 7.07 (d, J=8 Hz; 1H), 4.13-4.08 (m, 2H), 3.97 (s, 3H), 1.60-1.57 (m, 2H), 1.48-1.45 (m, 2H), 1.13 (t, J=7.4 Hz; 3H) ppm.

Workup

  1. additionAfter addition the reaction mixture
  2. washwashed with water (100 mL×2), brine (50 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified by silica gel column chromatography (0 to 10% EtOAc in dichloromethane as eluent)

Sources & evidence

ORD record
ord-26d8611e15904b4bba675d14af505b4b
Source dataset
uspto-grants-2015_11
Patent number
US09181248B2

Linked notes

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