1-Boc-3-methylpyrazole-5-boronic acid → 5-{2-[4-(1-Tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridin-6-yl}-3-methyl-pyrazole-1-carboxylic acid tert-butyl ester

HRID 872358Notes

Reaction equation

HRID 872358 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[CH:25]=[CH:24][C:23](Br)=[CH:22][N:21]4[C:27]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:35]([O:39][C:40]([N:42]1[C:46](B(O)O)=[CH:45][C:44]([CH3:50])=[N:43]1)=[O:41])([CH3:38])([CH3:37])[CH3:36]>O1CCOCC1.O>[C:35]([O:39][C:40]([N:42]1[C:46]([C:23]2[CH:24]=[CH:25][C:20]3[N:21]([C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[C:18]([C:15]4[CH:16]=[CH:17][C:12]([C:8]5([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:34])[CH2:11][CH2:10][CH2:9]5)=[CH:13][CH:14]=4)[N:19]=3)[CH:22]=2)=[CH:45][C:44]([CH3:50])=[N:43]1)=[O:41])([CH3:38])([CH3:37])[CH3:36]

Participants

5

Reactant 2

HCID 532163261-Boc-3-methylpyrazole-5-boronic acidHCID 66665495Tert-butyl {1-[4-(6-bromo-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutyl}carbamate

Product 1

HCID 666655825-{2-[4-(1-Tert-butoxycarbonylamino-cyclobutyl)-phenyl]-3-phenyl-imidazo[1,2-a]pyridin-6-yl}-3-methyl-pyrazole-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of {1-[4-(6-bromo-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (50 mg) and 1-tert-butoxycarbonyl-3-methylpyrazole-5-boronic acid (44 mg) in dioxane (1 mL) and water (0.43 mL) was placed under argon and [1,1-bis-(diphenylphosphino)-ferrocene]-dichloropalladium-dichlormethane-complex (7.9 mg) added. The mixture was heated at 110° C. under microwave irradiation for 60 minutes. On cooling the mixture was partitioned between DCM and water and extracted. The organic portion was dried and concentrated in vacuo to give the crude title compound which was used in the next step without further purification.

Workup

  1. temperatureOn cooling the mixture
  2. customwas partitioned between DCM and water
  3. extractionextracted
  4. customThe organic portion was dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bfbd258b9d674939b6fcf0161124845b
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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