Potassium Carbonate → N-[[2-chloro-5-[1-(3,4-dihydro-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]formamide

HRID 1408423Notes

Reaction equation

HRID 1408423 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)=[CH:4][C:3]=1[CH2:13][NH:14][CH:15]=[O:16].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+].I[C:34]1[CH:35]=[CH:36][C:37]2[O:42][CH2:41][CH2:40][CH2:39][C:38]=2[CH:43]=1>O1CCOCC1.[Cu]I>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][N:10]([C:34]3[CH:35]=[CH:36][C:37]4[O:42][CH2:41][CH2:40][CH2:39][C:38]=4[CH:43]=3)[N:9]=2)=[CH:4][C:3]=1[CH2:13][NH:14][CH:15]=[O:16]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 109451636-IodochromanHCID 178522771HCID 178522771, compound2×

Product 1

HCID 86668919N-[[2-chloro-5-[1-(3,4-dihydro-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]formamide

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of N-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]methyl]formamide (i.e. the product of Step D) (0.25 g, 1.1 mmol) in dioxane (2.5 mL) was added trans-N,N′-dimethylcyclohexane-1,2-diamine (0.06 mL, 0.43 mmol) followed copper(I) iodide (0.08 g, 0.43 mmol), potassium carbonate (0.87 g, 6.4 mmol) and 3,4-dihydro-6-iodo-2H-1-benzopyran (0.45 g, 1.7 mmol; prepared according to the procedure of Muraki et al., Tetrahedron Lett. 1996, 37, 2441). The reaction mixture was heated at 110° C. for 20 h and then cooled to ambient temperature. The solvent was evaporated, and the residue was taken up in chloroform, washed with water and brine, then dried (Na2SO4) and concentrated. The crude residue was then purified by preparative TLC (2% methanol in chloroform as eluant) to provide the title product, a compound of the present invention, as a solid (0.069 g).

Workup

  1. customprepared
  2. temperaturecooled to ambient temperature
  3. customThe solvent was evaporated
  4. washwashed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude residue was then purified by preparative TLC (2% methanol in chloroform as eluant)

Sources & evidence

ORD record
ord-3f511870d6af46aea7cfd48c12963e11
Source dataset
uspto-grants-2014_12
Patent number
US08921360B2

Reaction notes

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