Pyridine → 1,1-Dimethylethyl 2-(4-cyanophenyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate

HRID 1364114Notes

Reaction equation

HRID 1364114 reaction equation
[N:1]1[NH:2][CH:3]=[C:4]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6][C:5]=12.[C:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)#[N:19].N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:18]([C:20]1[CH:25]=[CH:24][C:23]([N:2]2[CH:3]=[C:4]3[C:5]([CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10]3)=[N:1]2)=[CH:22][CH:21]=1)#[N:19]

Participants

6

Reactant 3

HCID 1049PyridineHCID 27343264-Cyanophenylboronic acidHCID 178451637HCID 178451637, compound

Product 1

HCID 669307651,1-Dimethylethyl 2-(4-cyanophenyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate (may be prepared as described in Description 9) (1.80 g, 7.58 mmol), 4-cyanophenyl boronic acid (2.23 g, 15.16 mmol; commercially available from e.g. Aldrich), copper(II) acetate (4.15 g, 22.76 mmol), pyridine (1.21 ml, 15.16 mmol) and powdered 4 Å molecular sieves (5.33 g) were stirred in dichloromethane (80 ml) at room temperature in air for 40 hours. The mixture was filtered through a pad of Kieselguhr and the filtrate evaporated. The residue was dissolved in ethyl acetate and the solution washed with 5% sodium bicarbonate solution (×3), dried over magnesium sulphate and evaporated. The residue was purified by flash chromatography eluting with 10-40% ethyl acetate in n-pentane to give the title compound (D10). MS (ES+) m/e 339 [M+H]+

Workup

  1. filtrationThe mixture was filtered through a pad of Kieselguhr
  2. customthe filtrate evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution washed with 5% sodium bicarbonate solution (×3)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 10-40% ethyl acetate in n-pentane

Sources & evidence

ORD record
ord-bf9f76de2df64c078bcf924e2d0db329
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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