Sodium Carbonate → HCID 66744145, compound

HRID 1959350Notes

Reaction equation

HRID 1959350 reaction equation
Br[C:2]1[N:3]=[C:4]([C:9]2[NH:13][C:12]3[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:11]=3[N:10]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:27]2[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][CH:32]=2)O1.C(P(CC)CC)C.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.Cl[Pd]Cl.CCOC(C)=O>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH:28]=2)=[N:3][C:4]=1[C:9]1[NH:13][C:12]2[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:11]=2[N:10]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27365TriethylphosphineHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 580842975-bromo-3-(6-methyl-1H-benzo[d]imidazol-2-yl)pyrazin-2-amine

Product 1

HCID 66744145HCID 66744145, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-bromo-3-(6-methyl-1H-benzimidazol-2-yl)pyrazin-2-amine (500 mg, 1.644 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate (660.8 mg, 2.137 mmol), dichloropalladium; triethylphosphane (34.00 mg, 0.08220 mmol) and Na2CO3 (2.466 mL of 2 M, 4.932 mmol) in DMF (5.000 mL) were heated to 130° C. for 60 min in a microwave. EtOAc was added and the organic phase washed with saturated aqueous Na2CO3, dried (MgSO4) and concentrated in vacuo. The mixture was taken through crude to the next stage. MS (ES+) 407

Workup

  1. washthe organic phase washed with saturated aqueous Na2CO3
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2e9c036339c64b91ac5ca599bcc77feb
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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