Potassium Carbonate → HCID 131727922, compound

HRID 2242656Notes

Reaction equation

HRID 2242656 reaction equation
[F:1][C:2]1([F:39])[CH2:6][CH2:5][N:4]([C:7]([C@@H:9]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C@H:10]([CH:16]2[CH2:21][CH2:20][C:19](B3OC(C)(C)C(C)(C)O3)=[CH:18][CH2:17]2)[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[O:8])[CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Br[C:47]1[CH:48]=[CH:49][C:50]2[N:51]([N:53]=[CH:54][N:55]=2)[CH:52]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:34]([O:33][C:32](=[O:38])[NH:31][C@H:9]([C:7]([N:4]1[CH2:5][CH2:6][C:2]([F:1])([F:39])[CH2:3]1)=[O:8])[C@H:10]([CH:16]1[CH2:21][CH2:20][C:19]([C:47]2[CH:48]=[CH:49][C:50]3[N:51]([N:53]=[CH:54][N:55]=3)[CH:52]=2)=[CH:18][CH2:17]1)[C:11]([N:13]([CH3:14])[CH3:15])=[O:12])([CH3:37])([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 115139346-Bromo-(1,2,4)triazolo(1,5-a)pyridineHCID 91550700HCID 91550700, compound

Product 1

HCID 131727922HCID 131727922, compound

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
80 °C

Procedure

The material from Step B (2.0 g, 3.6 mmol) was combined with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.43 g, 0.53 mmol), potassium carbonate (1.5 g, 11 mmol), and 6-bromo[1,2,4]triazolo[1,5-a]pyridine (80% pure, 1.1 g, 4.3 mmol) and the flask was flushed with nitrogen. DMF (35 mL) was added, and the resulting mixture was heated at 80° C. for 14 h. The reaction mixture was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were washed with brine, dried (anhydrous sodium sulfate), and concentrated in vacuo. The residue was purified by silica gel chromatography twice (0-5% methanol in dichloromethane, then 0-5% methanol in ethyl acetate) to afford the title compound. LC/MS 547.3 (M+1).

Workup

  1. customthe flask was flushed with nitrogen
  2. additionDMF (35 mL) was added
  3. additionThe reaction mixture was diluted with ethyl acetate
  4. washwashed with water
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washthe combined organic extracts were washed with brine
  7. dry with materialdried (anhydrous sodium sulfate)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel chromatography twice (0-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-0d3bfa97051647768942898c829e63a5
Source dataset
uspto-grants-2010_03
Patent number
US07671073B2

Reaction notes

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