tert-Butanol → Tert-butyl 3-(imidazo[1,2-b]pyridazin-2-yl)phenylcarbamate

HRID 251825Notes

Reaction equation

HRID 251825 reaction equation
[N:1]1[C:2]([C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)C(O)=O)=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[N:5]2.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])=CC=1.CC[N:38]([CH2:41]C)CC.[CH3:43][C:44]([OH:47])([CH3:46])[CH3:45]>C1(C)C=CC=CC=1.O>[N:1]1[C:2]([C:10]2[CH:11]=[C:12]([NH:38][C:41](=[O:26])[O:47][C:44]([CH3:46])([CH3:45])[CH3:43])[CH:16]=[CH:17][CH:18]=2)=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[N:5]2

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 576868123-(Imidazo[1,2-b]pyridazin-2-yl)benzoic acid

Product 1

HCID 57686824Tert-butyl 3-(imidazo[1,2-b]pyridazin-2-yl)phenylcarbamateYield 38.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 3-(imidazo[1,2-b]pyridazin-2-yl)benzoic acid (1 mmol), DPPA (3 mmol) and Et3N (3 mmol) in toluene was heated to reflux for 4 h. Then t-BuOH (1 ml) was added and reflux was continued overnight. Water was added, and the mixture was extracted with EtOAc. The organic layer was washed with diluted HCl, brine and NaHCO3 (aq), and was concentrated to give a solid. After purification by chromatography, tert-butyl 3-(imidazo[1,2-b]pyridazin-2-yl)phenylcarbamate was obtained with a yield of 38.5%.

Workup

  1. temperatureto reflux for 4 h
  2. temperaturereflux
  3. extractionthe mixture was extracted with EtOAc
  4. washThe organic layer was washed with diluted HCl, brine and NaHCO3 (aq)
  5. concentrationwas concentrated
  6. customto give a solid
  7. customAfter purification by chromatography

Sources & evidence

ORD record
ord-f6d90c18b4634b25988bd7cb889cefb5
Source dataset
uspto-grants-2011_01
Patent number
US07868001B2

Reaction notes

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