HCID 69236174, compound → HCID 69232624, compound

HRID 1593643Notes

Reaction equation

HRID 1593643 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]3[CH2:10][CH2:11][CH:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][C:7]=3[C:6]=2[CH:19]=1.[C:20]([Cu])#[N:21]>CN1CCCC1=O>[C:20]([C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]3[CH2:10][CH2:11][CH:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][C:7]=3[C:6]=2[CH:19]=1)#[N:21]

Participants

4

Reactant 2

HCID 69236174HCID 69236174, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 69232624HCID 69232624, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

To a solution of ethyl 8-bromo-1,2,3,4-tetrahydrodibenzo[b,d]thiophene-2-carboxylate (0.62 g, 1.83 mmol) in 10 mL 1-methylpyrrolidin-2-one was added CuCN (0.328 g, 3.66 mmol). The reaction was heated at 170° C. overnight, then was cooled to room temperature and was partitioned between EtOAc and water. The organic layer was washed with water, then brine, then dried over MgSO4, filtered and concentrated. Purification by chromatography on silica gel (25% EtOAc in hexane) afforded 0.46 g (88%) of the title compound as a white solid: mp 121-122° C.; MS (ES) m/z=285 [M]+.

Workup

  1. temperaturewas cooled to room temperature
  2. customwas partitioned between EtOAc and water
  3. washThe organic layer was washed with water
  4. dry with materialbrine, then dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by chromatography on silica gel (25% EtOAc in hexane)

Sources & evidence

ORD record
ord-14b4b8085eb743e281ca62c0d2f82582
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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