HCID 89601195, compound → HCID 89601788, compound

HRID 514215Notes

Reaction equation

HRID 514215 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]2[C:10](=[O:23])/[C:11](=[CH:16]/[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)/[CH2:12][C:13]=2[O:14][CH3:15])=[C:4]([Cl:24])[CH:3]=1>CC(O)=O.CCOC(C)=O.[Zn]>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]2[C:10](=[O:23])[CH:11]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:12][C:13]=2[O:14][CH3:15])=[C:4]([Cl:24])[CH:3]=1

Participants

5

Reactant 1

HCID 89601195HCID 89601195, compound

Product 1

HCID 89601788HCID 89601788, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (5E)-2-(4-bromo-2,6-dichloro-phenyl)-3-methoxy-5-(2-pyridylmethylene)cyclopent-2-en-1-one (235 mg, 0.55 mmol) in glacial AcOH (2.4 ml) at 0°C. was added zinc dust (126 mg, 1.94 mmol) portionwise over 10 minutes. The reaction was stirred at room temperature for 2 hours and then diluted with EtOAc (25 ml), filtered through Celite and washed through with further EtOAc (2×20 ml). The filtrate was evaporated to dryness under reduced pressure and then azeotroped with toluene and then MeOH to give the desired product (235 mg, 99%) as a brown gum. 1H NMR (400 MHz, CDCl3) δ ppm 8.52 (d, 1H), 7.60 (dd, 1H), 7.45 (2×s, 2×1H), 7.25 (d, 1H), 7.15 (dd, 1H), 3.80 (s, 3H), 3.45-3.35 (1H, m), 3.20-3.10 (m, 1H), 3.00-2.90 (1H, m), 2.90-2.85 (m, 2H).

Workup

  1. filtrationfiltered through Celite
  2. washwashed through with further EtOAc (2×20 ml)
  3. customThe filtrate was evaporated to dryness under reduced pressure
  4. customazeotroped with toluene

Sources & evidence

ORD record
ord-cafd8d6a64564351a42a195a6229a4c1
Source dataset
uspto-grants-2015_08
Patent number
US09107415B2

Reaction notes

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