tert-Butanol → HCID 67041776, compound

HRID 908205Notes

Reaction equation

HRID 908205 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[C:18]1([C:24]2[N:25]=[C:26]3[CH:31]=[C:30](C(O)=O)[CH:29]=[CH:28][N:27]3[CH:35]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([N:38]([CH2:41]C)CC)C.[C:43]([OH:47])([CH3:46])([CH3:45])[CH3:44]>C(OCC)(=O)C>[C:43]([O:47][C:41](=[O:8])[NH:38][C:30]1[CH:29]=[CH:28][N:27]2[CH:35]=[C:24]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:25]=[C:26]2[CH:31]=1)([CH3:46])([CH3:45])[CH3:44]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 3525732-Phenylimidazo[1,2-a]pyridine-7-carboxylic acid

Product 1

HCID 67041776HCID 67041776, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under an atmosphere of argon, diphenylphosphoryl azide (8.16 g, 27 mmol) was added to a solution of 2-phenyl-imidazo[1,2-a]pyridine-7-carboxylic acid (6.36 g, 27 mmol) and triethylamine (5.40 g, 53 mmol) in tert-butanol (100 ml). The mixture was heated to reflux overnight, then cooled and diluted with ethyl acetate (100 ml). The mixture was filtered, and the filtrate was washed (NH4Cl satd., water, brine), and dried (Na2SO4). The title compound (4.81 g, 55%) was isolated from the residue by column chromatography (silica gel, CH2Cl2:MeOH=100:0-60:40). MS (m/e)=254.2 [M-Boc+H+].

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. temperaturecooled
  4. filtrationThe mixture was filtered
  5. washthe filtrate was washed (NH4Cl satd., water, brine)
  6. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-12f64d24e82d478bb17124cc188ed683
Source dataset
uspto-grants-2011_09
Patent number
US08017604B2

Reaction notes

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