HCID 67368012, compound → HCID 67366331, compound

HRID 1184963Notes

Reaction equation

HRID 1184963 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[O:8][C:7]([C:14]([F:17])([F:16])[F:15])=[C:6]([C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1)[C:5]2=[O:28].[C:29]([Cu])#[N:30]>CN1C(=O)CCC1>[C:29]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[O:8][C:7]([C:14]([F:17])([F:16])[F:15])=[C:6]([C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1)[C:5]2=[O:28])#[N:30]

Participants

4

Reactant 2

HCID 67368012HCID 67368012, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 67366331HCID 67366331, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of methyl 4-(6-bromo-7-methoxy-4-oxo-2-(trifluoromethyl)-4H-chromen-3-yl)benzoate (350 mg, 0.76 mmol) in NMP (3 mL) was added CuCN (340 mg, 3.8 mmol). The mixture was stirred at 150° C. for 8 h under the protection of nitrogen. The mixture was cooled to room temperature and quenched with water (10 mL) and filtered. The cake was washed with acetone (15 mL×2). The filtrate was concentrated in vacuo to give brown oil, which was purified by prep-TLC (PE/EA=5/1) to give product (125 mg, 40%) as a yellow solid. MS (ESI): 404.0 [M+1]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched with water (10 mL)
  3. filtrationfiltered
  4. washThe cake was washed with acetone (15 mL×2)
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give brown oil, which
  7. customwas purified by prep-TLC (PE/EA=5/1)

Sources & evidence

ORD record
ord-1a19b88712364f12a5c8e38db0e764a2
Source dataset
uspto-grants-2014_03
Patent number
US08669381B2

Reaction notes

Loading…