Potassium Phosphate, Tribasic → HCID 86685332, compound

HRID 1853062Notes

Reaction equation

HRID 1853062 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([C:13]3([CH2:24][C:25]#[N:26])[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]3)[CH:12]=2)[N:5]2[CH:27]=[CH:28][N:29]=[C:4]2[CH:3]=1.[F:30][C:31]([F:42])([F:41])[C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[C:25]([CH2:24][C:13]1([N:11]2[CH:12]=[C:8]([C:6]3[N:5]4[CH:27]=[CH:28][N:29]=[C:4]4[CH:3]=[C:2]([C:35]4[CH:36]=[CH:37][C:32]([C:31]([F:42])([F:41])[F:30])=[CH:33][CH:34]=4)[N:7]=3)[CH:9]=[N:10]2)[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]1)#[N:26]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86685321HCID 86685321, compound

Product 1

HCID 86685332HCID 86685332, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

To a vial charged with tert-butyl 3-(4-(7-chloroimidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-3-(cyanomethyl)azetidine-1-carboxylate (Preparation N; 490 mg; 1.18 mmol); 4-(trifluoromethyl)phenylboronic acid (337 mg; 1.78 mmol); Pd2dba3 (108 mg; 0.118 mmol); XPHOS (113 mg; 0.237 mmol) and potassium phosphate (3.55 mmol; 2M aqueous solution) was added 1,4-dioxane (10 mL). The mixture was sparged with nitrogen for 15 minutes. The vial was then sealed and heated for 3 hours at 75° C. with magnetic stirring. The mixture was diluted with methylene chloride (20 mL) and aqueous sodium bicarbonate solution (20 mL) was added. The mixture was extracted into methylene chloride (2×20 mL). The combined organic extracts were dried over magnesium sulfate, filtered and evaporated under reduced pressure. The resulting materiel was triturated with ether and the solids were collected and dried under vacuum to give the desired product as an off white solid (410 mg). MS (apci) m/z=524.2 (M+H).

Workup

  1. customThe mixture was sparged with nitrogen for 15 minutes
  2. customThe vial was then sealed
  3. additionThe mixture was diluted with methylene chloride (20 mL) and aqueous sodium bicarbonate solution (20 mL)
  4. additionwas added
  5. extractionThe mixture was extracted into methylene chloride (2×20 mL)
  6. dry with materialThe combined organic extracts were dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe resulting materiel was triturated with ether
  10. customthe solids were collected
  11. customdried under vacuum

Sources & evidence

ORD record
ord-0fe707357e2f44e390805ef1be39a8be
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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