Sodium Carbonate → HCID 178510701, compound

HRID 227793Notes

Reaction equation

HRID 227793 reaction equation
Br[C:2]1[C:3]([C:14]#[N:15])=[N:4][N:5](C(OC(C)(C)C)=O)[CH:6]=1.CC1(C)C(C)(C)OB([C:24]2[C:25]([O:30][C:31]3[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=3)=[N:26][CH:27]=[CH:28][CH:29]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[NH2:37][C:34]1[CH:35]=[CH:36][C:31]([O:30][C:25]2[C:24]([C:2]3[C:3]([C:14]#[N:15])=[N:4][NH:5][CH:6]=3)=[CH:29][CH:28]=[CH:27][N:26]=2)=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 574164444-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yloxy)benzenamineHCID 66732252tert-butyl 4-bromo-3-cyano-1H-pyrazole-1-carboxylate

Product 1

HCID 178510701HCID 178510701, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Dioxane (2.0 mL) was added to a 20 mL sealed tube. The tube was purged with nitrogen for 5 minutes. To this was added tert-butyl 4-bromo-3-cyano-1-H-pyrazole-1-carboxylate (0.100 g, 0.368 mmol), 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yloxy)benzenamine (0.229 g, 0.735 mmol), and sodium carbonate (2.0 M in water)(0.667 mL). Palladium(II) acetate (0.008 g, 0.037 mmol) and tri-t-butylphosphonium tetrafluoroborate (0.021 g, 0.074 mmol) was added and the tube was purged with nitrogen, sealed, and heated to 100° C. for 17 hours. The reaction was cooled to RT, concentrated and passed through a pad of silica with the aid of 90:10:1 (CH2Cl2:MeOH:NH4OH). The eluent was concentrated to yield 4-(2-(4-aminophenoxy)pyridin-3-yl)-1-H-pyrazole-3-carbonitrile as light brown solid. MS m/z=278 [M+1]+. Calc'd for Cl5H11N5O: 277.28.

Workup

  1. customsealed tube
  2. customThe tube was purged with nitrogen for 5 minutes
  3. customthe tube was purged with nitrogen
  4. customsealed
  5. temperatureThe reaction was cooled to RT
  6. concentrationconcentrated
  7. concentrationThe eluent was concentrated

Sources & evidence

ORD record
ord-0dbb14f7a1bf4e19ad7e1ab1dbb4451b
Source dataset
uspto-grants-2009_07
Patent number
US07560551B2

Reaction notes

Loading…