Potassium Phosphate, Tribasic → HCID 24855712, compound

HRID 422565Notes

Reaction equation

HRID 422565 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]1([C:15]([F:18])([F:17])[F:16])[CH2:14][CH2:13]1)=[N:7][N:6]=[CH:5]2.[CH:19]1([NH:22][C:23](=[O:40])[C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26](B3OC(C)(C)C(C)(C)O3)[CH:25]=2)[CH2:21][CH2:20]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>O1CCOCC1.O.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]>[CH:19]1([NH:22][C:23](=[O:40])[C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[C:8]([C:12]3([C:15]([F:18])([F:17])[F:16])[CH2:14][CH2:13]3)=[N:7][N:6]=[CH:5]4)[CH:25]=2)[CH2:20][CH2:21]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 666751956-Chloro-1-[1-(trifluoromethyl)cyclopropyl]phthalazine

Product 1

HCID 24855712HCID 24855712, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 6-chloro-1-(1-(trifluoromethyl)cyclopropyl)phthalazine (20 mg, 73 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (27 mg, 88 μmol), Pd2(dba)3 (2.0 mg, 2.2 μmol), potassium phosphate (47 mg, 220 μmol) and X-Phos (2.0 mg) in 1.0 mL of dioxane and 0.5 mL water in a sealed glass tube was heated in a microwave for 20 min at 135° C. The mixture was partitioned between 1.0 N NaOH (1.0 mL) and EtOAc (5.0 mL). The organic layer was separated, dried and concentrated. Purification on an ISCO (4.0 g column, 60-100% EtOAc:Hexanes) provided the title compound as a yellow amorphous solid. MS (ESI, pos. ion) m/z: 412.1 (M+1).

Workup

  1. customThe mixture was partitioned between 1.0 N NaOH (1.0 mL) and EtOAc (5.0 mL)
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated
  5. customPurification on an ISCO (4.0 g column, 60-100% EtOAc:Hexanes)

Sources & evidence

ORD record
ord-fcded0c490704710b114fa357c22db69
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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