Ethyl chloroformate → HCID 11353129, compound

HRID 347365Notes

Reaction equation

HRID 347365 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[C:11]([O:32][CH3:33])=[CH:12][C:13]([O:30][CH3:31])=[C:14](/[CH:16]=[CH:17]/[C:18]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[O:19])[CH:15]=1.Cl[C:35]([O:37][CH2:38][CH3:39])=[O:36].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:38]([O:37][C:35]([NH:29][S:26]([C:23]1[CH:22]=[CH:21][C:20]([C:18](=[O:19])/[CH:17]=[CH:16]/[C:14]2[CH:15]=[C:10]([C:2]3[NH:1][C:9]4[C:4]([CH:3]=3)=[CH:5][CH:6]=[CH:7][CH:8]=4)[C:11]([O:32][CH3:33])=[CH:12][C:13]=2[O:30][CH3:31])=[CH:25][CH:24]=1)(=[O:28])=[O:27])=[O:36])[CH3:39]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 210416274-{3E-[5-(1H-indol-2-yl)-2,4-dimethoxyphenyl]acryloyl}benzenesulfonamide

Product 1

HCID 11353129HCID 11353129, compoundYield 0.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-{3E-[5-(1H-indol-2-yl)-2,4-dimethoxyphenyl]acryloyl}benzenesulfonamide (Ex-35E, 3.0 g, 6.5 mmol) in 250 mL of acetone were added ethyl chloroformate (0.93 g, 8.6 mmol) and K2CO3 (2.3 g, 16.7 mmol). The mixture was heated to reflux overnight. The yellow precipitate-formed was filtered. The filtrate was acidified to pH=1 with 3N HCl and extracted with CH2Cl2. The organic phase was washed with water, dried over MgSO4, and concentrated. The residue was further purified by passing a short silica gel column eluted with EtOAc/hexenes (1:1) to give 30 mg of the title compound as a yellow solid, mp 165–175° C. 1H-NMR (300 MHz, CDCl3) δ 9.39 (br, 1H), 8.04–8.20 (m, 6H), 7.64 (d, J=7 Hz, 1H), 7.57 (d, J=15 Hz, 1H), 7.42 (d, J=8 Hz, 1H), 7.12–7.07(m, 2H), 6.87 (s, 1H), 6.59 (s, 1H), 4.16 (q, J=7 Hz, 2H), 4.10 (s, 3H), 4.01 (s, 3H), 1.24 (t, J=7 Hz, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customThe yellow precipitate-formed
  4. filtrationwas filtered
  5. extractionextracted with CH2Cl2
  6. washThe organic phase was washed with water
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was further purified
  10. washeluted with EtOAc/hexenes (1:1)

Sources & evidence

ORD record
ord-774aa4f5c3a74ea9bbd644fbc0dfb212
Source dataset
uspto-grants-2007_02
Patent number
US07173129B2

Reaction notes

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