HCID 178418546, compound → HCID 178510358, compound

HRID 1896504Notes

Reaction equation

HRID 1896504 reaction equation
Br[C:2]1[C:7]2[NH:8][C:9]3[CH:10]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:13][C:14]=3[C:6]=2[C:5]([OH:19])=[N:4][CH:3]=1.[C:20]([Cu])#[N:21]>CN1C(=O)CCC1>[OH:19][C:5]1[C:6]2[C:14]3[CH:13]=[CH:12][C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=3[NH:8][C:7]=2[C:2]([C:20]#[N:21])=[CH:3][N:4]=1

Participants

4

Reactant 2

HCID 178418546HCID 178418546, compoundHCID 178517584HCID 178517584, compound

Product 1

HCID 178510358HCID 178510358, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
225 °C

Procedure

A mixture of 4-bromo-7-(trifluoromethyl)-5H-pyrido[4,3-b]indol-1-ol, CuCN (1.4 equiv) in NMP (0.2 M) was heated in the microwave reactor at 225° C. for 40 min. The reaction mixture was then poured into EtOAc/hexanes (10/1) which was passed through a plug of silica gel and eluted with EtOAc. The EtOAc was evaporated and the resulting mixture was partitioned between EtOAc and brine. The organic phase was separated, dried over Na2SO4 and evaporated. The residue was suspended in EtOAc and hexanes, and was then filtered to provide the title compound.

Workup

  1. washeluted with EtOAc
  2. customThe EtOAc was evaporated
  3. customthe resulting mixture was partitioned between EtOAc and brine
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. filtrationhexanes, and was then filtered

Sources & evidence

ORD record
ord-0d268cc996364d15a2e5937868e914fe
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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