Potassium Phosphate, Tribasic → HCID 58063511, compound

HRID 2035725Notes

Reaction equation

HRID 2035725 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[N:10][N:11]([CH:13]3[CH2:19][CH2:18][C:17]4[C:20]([F:24])=[CH:21][CH:22]=[CH:23][C:16]=4[N:15]([CH2:25][C:26]([F:29])([F:28])[F:27])[C:14]3=[O:30])[CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33](B(O)O)[CH:32]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[F:24][C:20]1[C:17]2[CH2:18][CH2:19][CH:13]([N:11]3[CH:12]=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([C:33]5[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=5)[CH:3]=4)[N:9]=[N:10]3)[C:14](=[O:30])[N:15]([CH2:25][C:26]([F:29])([F:28])[F:27])[C:16]=2[CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27343783-Pyridinylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 66683136HCID 66683136, compound

Product 1

HCID 58063511HCID 58063511, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-[4-(3-Chlorophenyl)-1H-1,2,3-triazol-1-yl]-6-fluoro-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one (30 mg, 0.068 mmol), pyridin-3-ylboronic acid (12.67 mg, 0.103 mmol), palladium acetate (3.07 mg, 0.014 mmol), potassium phosphate tribasic (29.0 mg, 0.137 mmol), and S-Phos (8.42 mg, 0.021 mmol) were added to a microwave vial. The reactants were suspended in THF (414 μL) and H2O (41 μL) and the vial sealed. The reaction mixture was irradiated at 120° C. in the microwave for 10 minutes, The completed reaction was filtered and concentrated in vacuo. Analytically pure material was obtained by purification by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.05% Formic Acid. Lyophilisation afforded 6-fluoro-3-[4-(3-pyridin-3-ylphenyl)-1H-1,2,3-triazol-1-yl]-1-(2,2,2-trifluoroethyl)-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one.

Workup

  1. customThe reaction mixture was irradiated at 120° C. in the microwave for 10 minutes
  2. customThe completed reaction
  3. filtrationwas filtered
  4. concentrationconcentrated in vacuo
  5. customAnalytically pure material was obtained by purification by preparative HPLC Reverse phase (C-18)
  6. washeluting with acetonitrile/water+0.05% Formic Acid

Sources & evidence

ORD record
ord-d99d31a50c3b4235877b32ba94e69042
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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