HCID 59497680, compound → HCID 59497453, compound

HRID 1747458Notes

Reaction equation

HRID 1747458 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[C:7](Br)(Br)[C:8](=[O:15])[NH:9][C:10]=2[CH:11]=[C:12]([Br:14])[CH:13]=1)=[O:4]>C(O)(=O)C.C(OCC)(=O)C.[Zn]>[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH2:7][C:8](=[O:15])[NH:9][C:10]=2[CH:11]=[C:12]([Br:14])[CH:13]=1)=[O:4]

Participants

5

Reactant 1

HCID 59497680HCID 59497680, compound

Product 1

HCID 59497453HCID 59497453, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,3,6-Tribromo-2-oxo-2,3-dihydro-1H-indole-4-carboxylic acid methyl ester (5.90 g, 16.9 mmol) is suspended in glacial acetic acid (153 mL) and zinc dust (10 μM Mesh, 11.5 g, 169 mmol) is added over 5 minutes. The reaction is monitored by TLC and when complete (30 min) the reaction is filtered through celite and the filtrate washed with ethyl acetate. The combined filtrate and washings are evaporated in vacuo to yield an oil that is taken up in ethyl acetate (500 mL), washed with water (100 mL) and brine (100 mL). The organic layer is dried filtered and evaporated in vacuo to give the title compound that is recrystalized from ethyl acetate (2.2 g, 11.5 mmol 68%). LCMS (ESMS): m/z 271.3 (M+H+).

Workup

  1. customis monitored by TLC and when complete (30 min)
  2. filtrationis filtered through celite
  3. washthe filtrate washed with ethyl acetate
  4. customThe combined filtrate and washings are evaporated in vacuo
  5. customto yield an oil that
  6. washwashed with water (100 mL) and brine (100 mL)
  7. customThe organic layer is dried
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-9339d8c2573e498797d5e8487a1411f9
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

Loading…