Potassium Carbonate → HCID 12020642, compound

HRID 2415391Notes

Reaction equation

HRID 2415391 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:20][CH2:19][C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[NH:11][C:10]=3[CH:9]2[C:21]2[CH:22]=[CH:23][C:24]3[O:28][CH2:27][CH2:26][C:25]=3[CH:29]=2)=[N:6][CH:7]=1.[CH3:30][N:31]1[CH:35]=[CH:34][N:33]=[C:32]1[CH3:36].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:28]1[C:24]2[CH:23]=[CH:22][C:21]([CH:9]3[C:10]4[NH:11][C:12]5[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=5)[C:18]=4[CH2:19][CH2:20][N:8]3[C:5]3[N:4]=[CH:3][C:2]([C:35]4[N:31]([CH3:30])[C:32]([CH3:36])=[N:33][CH:34]=4)=[CH:7][N:6]=3)=[CH:29][C:25]=2[CH2:26][CH2:27]1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 156171,2-DimethylimidazoleHCID 11259399HCID 11259399, compound

Product 1

HCID 12020642HCID 12020642, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

2-(5-bromo-2-pyrimidinyl)-1-(2,3-dihydro-5-benzofuranyl)-2,3,4,9-tetrahydro-1H-β-carboline (0.45 g, 1.00 mmol), 1,2-dimethyl-1H-imidazole (0.18 g, 1.87 mmol), Pd(OAc)2 (12 mg, 0.05 mmol), PPh3 (26 mg, 0.1 mmol) and K2CO3 (0.28 g, 2 mmol) were stirred in 3.5 mL DMF at 140° C. for 14 hours. The mixture was poured into aqueous 10% NaOH solution (50 mL). The resulting solution was extracted with CH2Cl2 (3×50 mL) and dried over Na2SO4. Purification by preparative TLC yielded the title product as yellow powder.

Workup

  1. extractionThe resulting solution was extracted with CH2Cl2 (3×50 mL)
  2. dry with materialdried over Na2SO4
  3. customPurification by preparative TLC

Sources & evidence

ORD record
ord-0f2579a34ce842d8b905184a8a172d85
Source dataset
uspto-grants-2004_11
Patent number
US06818646B2

Reaction notes

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