tert-Butanol → (6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-yl)-carbamic acid tert-butyl ester

HRID 2382738Notes

Reaction equation

HRID 2382738 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[Br:18][C:19]1[C:20](C(O)=O)=[CH:21][C:22]2[N:23]([CH:25]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:27]=2)[CH:24]=1.C([N:39]([CH2:42]C)CC)C.[C:44]([OH:48])([CH3:47])([CH3:46])[CH3:45]>C(OCC)(=O)C>[C:44]([O:48][C:42](=[O:8])[NH:39][C:20]1[C:19]([Br:18])=[CH:24][N:23]2[CH:25]=[C:26]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:27]=[C:22]2[CH:21]=1)([CH3:47])([CH3:46])[CH3:45]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 670418506-Bromo-2-phenylimidazo[1,2-a]pyridine-7-carboxylic acid

Product 1

HCID 67041813(6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-yl)-carbamic acid tert-butyl esterYield 25%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under an atmosphere of argon, diphenylphosphoryl azide (8.20 g, 29 mmol) was added to a solution of 6-bromo-2-phenyl-imidazo[1,2-a]pyridine-7-carboxylic acid (9.16 g, 29 mmol) and triethylamine (5.8 g, 58 mmol) in tert-butanol (86 ml). The mixture was heated to reflux overnight, then cooled and diluted with ethyl acetate. The mixture was washed (NH4Cl satd.), and dried (Na2SO4). The title compound (2.75 g, 25%) was isolated from the residue by column chromatography (silica gel, heptane:ethyl acetate=100:0-50:50). MS (m/e)=388.1 [M+H+].

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. temperaturecooled
  4. washThe mixture was washed (NH4Cl satd.)
  5. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-2b668ff0a4c24db6ac7518a09533a7ad
Source dataset
uspto-grants-2012_09
Patent number
US08263584B2

Reaction notes

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