Potassium Phosphate, Tribasic → HCID 58243435, compound

HRID 2361689Notes

Reaction equation

HRID 2361689 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5](B2OC(C)(C)C(C)(C)O2)[CH:4]=[N:3]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[CH:35]1([N:39]2[CH2:45][CH2:44][CH2:43][N:42]([C:46]([N:48]3[CH2:51][CH:50]([O:52][C:53]4[CH:58]=[CH:57][C:56](I)=[CH:55][CH:54]=4)[CH2:49]3)=[O:47])[CH2:41][CH2:40]2)[CH2:38][CH2:37][CH2:36]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.ClCCl.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:35]1([N:39]2[CH2:45][CH2:44][CH2:43][N:42]([C:46]([N:48]3[CH2:49][CH:50]([O:52][C:53]4[CH:58]=[CH:57][C:56]([C:5]5[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=5)=[CH:55][CH:54]=4)[CH2:51]3)=[O:47])[CH2:41][CH2:40]2)[CH2:38][CH2:37][CH2:36]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 44476510HCID 44476510, compound

Product 1

HCID 58243435HCID 58243435, compoundYield 42.5%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (21 mg, 101 μmol), tricyclohexylphosphine (3.1 mg, 11 μmol) and Pd2(dba)3 (4.2 mg, 5 μmol) were dissolved in dioxane (0.25 ml) under a nitrogen atmosphere. Solid 1-cyclobutyl-4-{[3-(4-iodophenoxy)azetidin-1-yl]carbonyl}-1,4-diazepane (42 mg, 92 μmol) was added followed by K3PO4 (122 μl of a 1.27 M aqueous solution, 156 μmol). The reaction was stirred at room temperature for 30 minutes and then at 110° C. for 16 hours. The reaction was diluted with dichloromethane (30 ml), filtered through celite, washed twice with saturated NaHCO3 (15 ml), dried (MgSO4), filtered and concentrated at reduced pressure. The residue was purified by FCC (DCM/MeOH/NH3 with gradient, 98:2:1 to 90:10:1) and then recrystallised (Heptane/EtOAc) to give the title product as white solid (16 mg, 42%).

Workup

  1. waitat 110° C. for 16 hours
  2. filtrationfiltered through celite
  3. washwashed twice with saturated NaHCO3 (15 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was purified by FCC (DCM/MeOH/NH3 with gradient, 98:2:1 to 90:10:1)
  8. customrecrystallised (Heptane/EtOAc)

Sources & evidence

ORD record
ord-51a487a970114bcc97f80a2818d15839
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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