Potassium Carbonate → HCID 58300116, compound

HRID 79115Notes

Reaction equation

HRID 79115 reaction equation
Br[C:2]1[C:3]([N:9]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:10]1([N:9]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:2]3[CH:7]=[N:6][C:5]([NH2:8])=[N:4][C:3]2=3)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 58299674HCID 58299674, compound

Product 1

HCID 58300116HCID 58300116, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of compound 41 (0.35 g, 0.99 mmol), Pd(OAc)2 (33 mg, 0.15 mmol), (cyclohexyl)3PBF4 (110 mg, 0.30 mmol), and K2CO3 (138 mg, 0.10 mmol) in DMA (3 mL) was purged with N2 for 20 minutes and then heated at 160° C. for 3 hours. The reaction was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated. Purification by flash chromatography (ethyl acetate/hexane) gave compound 42 as a yellow solid (110 mg, 41%). LCMS-ESI (POS), M/Z, M+1: Found 267.1, Calculated 267.2.

Workup

  1. customwas purged with N2 for 20 minutes
  2. temperatureThe reaction was cooled to room temperature
  3. additiondiluted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification by flash chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-25504333584b411aa96eff03e352f1c1
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

Loading…