Dimethylformamide → (1-{4-[6-(2-Benzyloxy-pyridin-3-yl)-3-phenyl-imidazo[1,2-a]pyridin-2-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

HRID 872355Notes

Reaction equation

HRID 872355 reaction equation
CN(C=O)C.[C:6]([O:10][C:11](=[O:47])[NH:12][C:13]1([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[N:24]=[C:25]4[CH:30]=[CH:29][C:28](B5OC(C)(C)C(C)(C)O5)=[CH:27][N:26]4[C:40]=3[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[CH:19][CH:18]=2)[CH2:16][CH2:15][CH2:14]1)([CH3:9])([CH3:8])[CH3:7].[CH2:48]([O:55][C:56]1[C:61](Br)=[CH:60][CH:59]=[CH:58][N:57]=1)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[C:6]([O:10][C:11](=[O:47])[NH:12][C:13]1([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[N:24]=[C:25]4[CH:30]=[CH:29][C:28]([C:61]5[C:56]([O:55][CH2:48][C:49]6[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=6)=[N:57][CH:58]=[CH:59][CH:60]=5)=[CH:27][N:26]4[C:40]=3[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)=[CH:19][CH:18]=2)[CH2:14][CH2:15][CH2:16]1)([CH3:8])([CH3:7])[CH3:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 147124562-Benzyloxy-3-bromopyridineHCID 66665620(1-{4-[3-Phenyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-imidazo[1,2-a]pyridin-2-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

Product 1

HCID 66665949(1-{4-[6-(2-Benzyloxy-pyridin-3-yl)-3-phenyl-imidazo[1,2-a]pyridin-2-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To the crude DMF solution of the boronate from Step 1 was added 2-benzyloxy-3-bromopyridine (0.25 g), aqueous sodium carbonate solution (2M, 2.8 mL) and dioxane (4 mL) and the mixture placed under argon. [1,1-bis-(diphenylphosphino)-ferrocene]-dichloropalladium-dichlormethane-complex (0.070 mg) was added and the mixture heated at 110° C. under microwave irradiation for 30 minutes. On cooling the mixture was partitioned between DCM and water and extracted. The organic portion was washed with brine, dried and concentrated in vacuo. Purification was achieved by chromatography on silica gel to give the title compound (138 mg).

Workup

  1. temperatureOn cooling the mixture
  2. customwas partitioned between DCM and water
  3. extractionextracted
  4. washThe organic portion was washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customPurification

Sources & evidence

ORD record
ord-f68346fadb04410eb661446e52b9d0fc
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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