Water → 9-[8-(2,2,2-Trifluoro-acetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthene-3-carbonitrile

HRID 1987941Notes

Reaction equation

HRID 1987941 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[C:16]3[CH2:22][CH:21]4[N:23]([C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])[CH:18]([CH2:19][CH2:20]4)[CH2:17]3)[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[C:30]([Cu])#[N:31].O>CN(C=O)C>[F:27][C:25]([F:26])([F:28])[C:24]([N:23]1[CH:21]2[CH2:20][CH2:19][CH:18]1[CH2:17][C:16](=[C:6]1[C:5]3[CH:4]=[CH:3][C:2]([C:30]#[N:31])=[CH:15][C:14]=3[O:13][C:12]3[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:22]2)=[O:29]

Participants

5

Reactant 3

HCID 962WaterHCID 577253121-[3-(3-Bromoxanthen-9-ylidene)-8-aza-bicyclo[3.2.1]oct-8-yl]-2,2,2-trifluoroethanoneHCID 178418546HCID 178418546, compound

Product 1

HCID 577253399-[8-(2,2,2-Trifluoro-acetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthene-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Compound 5d (3 g, 6.46 mmol) in DMF (100 mL) was added CuCN (0.69 g, 7.70 mmol). The reaction mixture was refluxed for 2 d and then cooled to room temperature. The mixture was poured into water (100 mL), and extracted with EtOAc (3×100 mL). The combined organic layers were washed sequentially with H2O (100 mL), brine (100 mL), then dried (MgSO4) and concentrated. The crude product was purified by normal phase chromatography, using a gradient of ethyl acetate (0% to 10%) in heptane to give compound 5e. MS m/z (M+H+) 410.9; 1H NMR (CDCl3) δ 1.41 (m, 2H), 1.85 (m, 2H), 2.96 (m, 4H), 4.44 (m, 1H), 4.73 (m, 1H), 7.23 (m, 3H), 7.33 (m, 2H), 7.43 (dt, 1H), 7.51 (m, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 d
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organic layers were washed sequentially with H2O (100 mL), brine (100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by normal phase chromatography

Sources & evidence

ORD record
ord-e476545d02634e88b4a9f807a0b5e251
Source dataset
uspto-grants-2009_06
Patent number
US07553850B2

Reaction notes

Loading…