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

HRID 908221
Notes
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Reaction equation

HRID 908221 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-63b26d619cc942f9b25f071a29566cf8
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08017604B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes