Sodium Carbonate → 1-[2-(2-Isopropyl-2H-tetrazol-5-yl)-ethyl]-3-(6-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl)-urea

HRID 555979Notes

Reaction equation

HRID 555979 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:17]1[CH:18]=[CH:19][C:20]2[N:21]([CH:23]=[C:24]([NH:26][C:27]([NH:29][CH2:30][CH2:31][C:32]3[N:33]=[N:34][N:35]([CH:37]([CH3:39])[CH3:38])[N:36]=3)=[O:28])[N:25]=2)[CH:22]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].COCCOC>[CH:37]([N:35]1[N:34]=[N:33][C:32]([CH2:31][CH2:30][NH:29][C:27]([NH:26][C:24]2[N:25]=[C:20]3[CH:19]=[CH:18][C:17]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[CH:22][N:21]3[CH:23]=2)=[O:28])=[N:36]1)([CH3:39])[CH3:38]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 592518731-(6-Bromo-imidazo[1,2-a]pyridin-2-yl)-3-[2-(2-isopropyl-2H-tetrazol-5-yl)-ethyl]-urea2×

Product 1

HCID 251759421-[2-(2-Isopropyl-2H-tetrazol-5-yl)-ethyl]-3-(6-pyridin-3-yl-imidazo[1,2-a]pyridin-2-yl)-urea

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A microwave vial is charged with pyridine-3-boronic acid (0.031 g, 0.25 mmol), 2M aqueous sodium carbonate (1 ml) and DME (3 ml) and then purged with Argon for 30 minutes at room temperature. 1-(6-Bromo-imidazo[1,2-a]pyridin-2-yl)-3-[2-(2-isopropyl-2H-tetrazol-5-yl)-ethyl]-urea (Intermediate E1)(0.05 g, 0.13 mmol) and [1,1′-Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.016 g, 0.02 mmol) are added and the reaction mixture is heated using microwave radiation at 100° C. for 30 minutes. The reaction mixture is filtered through Celite® (filter agent) and washed through with EtOAc. The crude product is absorbed on silica and purified by flash chromatography, eluting with methanol in DCM (3%) to afford the title compound.

Workup

  1. custompurged with Argon for 30 minutes at room temperature
  2. temperaturethe reaction mixture is heated
  3. customat 100° C.
  4. customfor 30 minutes
  5. filtrationThe reaction mixture is filtered through Celite® (filter agent)
  6. washwashed through with EtOAc
  7. customThe crude product is absorbed on silica
  8. custompurified by flash chromatography
  9. washeluting with methanol in DCM (3%)

Sources & evidence

ORD record
ord-8bd4e6d8bce34af1ba34720cfe4f5f5d
Source dataset
uspto-grants-2011_11
Patent number
US08053574B2

Reaction notes

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