Sodium Carbonate → HCID 178448431, compound

HRID 1966728Notes

Reaction equation

HRID 1966728 reaction equation
Br[C:2]1[CH:25]=[CH:24][C:5]2[N:6]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]3[N:19]=[CH:18][NH:17][N:16]=3)=[N:8][C:4]=2[CH:3]=1.[NH2:26][C:27]1[N:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][N:28]=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:20]([N:6]1[C:5]2[CH:24]=[CH:25][C:2]([C:30]3[CH:29]=[N:28][C:27]([NH2:26])=[N:32][CH:31]=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]=[CH:18][NH:17][N:16]=1)([CH3:21])([CH3:22])[CH3:23]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 178448430HCID 178448430, compound

Product 1

HCID 178448431HCID 178448431, compoundYield 34.1%

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-(1H-1,2,4-triazol-3-yl)-phenyl]-1H-benzimidazole (80 mg, 0.2 mmol) in DMF (3.5 mL), follow by the addition of 2-aminopyrimidine-5-boronic acid pinacol ester (49 mg, 0.22 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, filtered and concentrated. The residue is loaded onto 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 (28 mg, 34%) as a pale-white solid. LCMS (ESMS): m/z 411.80 (M++1)

Workup

  1. washwashed with brine
  2. customdried under Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  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-0ef3489d4b9640fd9508920858e04f58
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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