Ethyl Acetate → HCID 178517584, compound

HRID 1896503Notes

Reaction equation

HRID 1896503 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[C:15]([OH:16])=[N:14][CH:13]=[CH:12][C:8]=3[NH:9][C:10]=2[CH:11]=1.[Br:19]Br.CCOC(C)=O.C([O-])(O)=O.[Na+]>CC(O)=O.ClCCl.[Zn]>[Br:19][C:12]1[C:8]2[NH:9][C:10]3[CH:11]=[C:3]([C:2]([F:1])([F:17])[F:18])[CH:4]=[CH:5][C:6]=3[C:7]=2[C:15]([OH:16])=[N:14][CH:13]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 24408BromineHCID 516892Sodium BicarbonateHCID 178517696HCID 178517696, compound

Product 1

HCID 178517584HCID 178517584, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 7-(trifluoromethyl)-5H-pyrido[4,3-b]indol-1-ol in AcOH (0.3 M) in a cold water bath was added a solution (0.3 M) of Br2 (1 equiv) in dichloromethane to provide a homogeneous mixture. After standing at room temperature a precipitate formed, and Zn powder (excess) was added at 0° C. After a period of 10 min, the reaction mixture was poured over EtOAc and saturated NaHCO3. The organic phase was separated, dried over Na2SO4 and evaporated. The resulting solid was suspended in ether and hexanes, and was then collected by filtration.

Workup

  1. customto provide a homogeneous mixture
  2. customAfter standing at room temperature
  3. customformed
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. filtrationhexanes, and was then collected by filtration

Sources & evidence

ORD record
ord-cd3c6a006a5341e0ad562291e9c69bf7
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

Loading…