Potassium Acetate → HCID 59351234, compound

HRID 555897Notes

Reaction equation

HRID 555897 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][C:3]1=[O:17].[NH:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[C:27]([C:29]1[CH:34]=[CH:33][C:32]([O:35][C:36]2[C:41](Cl)=[N:40][CH:39]=[CH:38][N:37]=2)=[CH:31][CH:30]=1)=[O:28].C([O-])(=O)C.[K+].O1CCOCC1.O>C(Cl)Cl.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>[NH:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[C:27]([C:29]1[CH:34]=[CH:33][C:32]([O:35][C:36]2[C:41]([C:5]3[CH2:6][CH2:7][N:2]([CH3:1])[C:3](=[O:17])[CH:4]=3)=[N:40][CH:39]=[CH:38][N:37]=2)=[CH:31][CH:30]=1)=[O:28]

Participants

7

Reactant 4

HCID 517044Potassium AcetateHCID 218864351,4-Dioxane--water (1/1)HCID 46207940(4-(3-chloropyrazin-2-yloxy)phenyl)(1H-benzo[d]imidazol-2-yl)methanoneHCID 59351291HCID 59351291, compound

Product 1

HCID 59351234HCID 59351234, compound

Reagents, catalysts & solvents 2

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)CatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-2(1H)-one (0.365 g, 1.539 mmol), (1H-benzo[d]imidazol-2-yl)(4-(3-chloropyrazin-2-yloxy)phenyl)methanone (0.540 g, 1.539 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.076 g, 0.108 mmol), potassium acetate (0.453 g, 4.62 mmol), and 9:1 dioxane-H2O (7.5 mL) were combined in a sealed tube and heated at 100° C. for 3 h. The cooled reaction was diluted with CH2Cl2 and washed with water; the aqueous layer was back-extracted with CH2Cl2 (1×). The organic extracts were combined, dried (MgSO4), filtered, and concentrated in vacuo. Flash column chromatography (1% to 5% MeOH/CH2Cl2) provided a crude crop of the desired product. Further trituration with MeOH afforded 4-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)-1-methyl-5,6-dihydropyridin-2(1H)-one as a yellow amorphous solid. [M+1]=426.8. IC50 (uM) +++++.

Workup

  1. customThe cooled reaction
  2. washwashed with water
  3. extractionthe aqueous layer was back-extracted with CH2Cl2 (1×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a7d417e8fef24553ac14ca81b5086093
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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