Sodium Carbonate → HCID 58541923, compound

HRID 1966731Notes

Reaction equation

HRID 1966731 reaction equation
Br[C:2]1[CH:26]=[CH:25][C:5]2[N:6]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]3[N:19]=[C:18]([CH3:20])[NH:17][N:16]=3)=[N:8][C:4]=2[CH:3]=1.[NH2:27][C:28]1[N:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][N:29]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOC(C)=O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[C:21]([N:6]1[C:5]2[CH:25]=[CH:26][C:2]([C:31]3[CH:30]=[N:29][C:28]([NH2:27])=[N:33][CH:32]=3)=[CH:3][C:4]=2[N:8]=[C:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:19]=[C:18]([CH3:20])[NH:17][N:16]=1)([CH3:23])([CH3:22])[CH3:24]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 58542054HCID 58542054, compound

Product 1

HCID 58541923HCID 58541923, compoundYield 25%

Reagents, catalysts & solvents 3

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a sealed vial is added 5-bromo-1-tert-butyl-2-[2-(5-methyl-1H-1,2,4-triazol-3-yl)-phenyl]-1H-benzimidazole (78 mg, 0.19 mmol) in DMF (3 mL), followed by the addition of 2-aminopyrimidine-5-boronic acid pinacol ester (50 mg, 0.226 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (20 mg, 0.028 mmol) and 2M aq. Na2CO3 (0.4 mL, 0.8 mmol). The reaction mixture is heated under Argon at 100° C. for 10 hours. The residue is diluted with EtOAc, washed with brine, dried under Na2SO4, is filtered and is concentrated. The residue is loaded to a silica gel column. The column is eluted with 0-8% 7M NH3 in MeOH/CH2Cl2. The product fractions are collected and concentrated to afford the title compound (20 mg, 25%) as a off-white solid. LCMS (ESMS): m/z 425.79 (M++1)

Workup

  1. washwashed with brine
  2. customdried under Na2SO4
  3. filtrationis filtered
  4. concentrationis concentrated
  5. washThe column is eluted with 0-8% 7M NH3 in MeOH/CH2Cl2
  6. customThe product fractions are collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6d34f561d5b14e2e910dcaaa1eea4d8c
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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