Ammonia → HCID 71239622, compound

HRID 873107Notes

Reaction equation

HRID 873107 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:19][OH:20])[CH:5]=[N:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1.[Cu][C:22]#[N:23].N>CN1CCCC1=O>[OH:20][CH2:19][C:4]1[CH:5]=[N:6][C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)=[C:2]([CH:3]=1)[C:22]#[N:23]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 71239626HCID 71239626, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 71239622HCID 71239622, compoundYield 107.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of (5-bromo-6-(3-(trifluoromethyl)phenoxy)pyridin-3-yl)methanol (530 mg, 1.522 mmol) in N-methyl-2-pyrrolidone (NMP) (5 mL) was added copper(I) cyanide (545 mg, 6.09 mmol). The reaction mixture was stirred at 150° C. for 24 h, then poured into aq. NH3 (100 mL) and extracted with ethyl acetate (100 mL). Separated organic part was washed with brine (100 mL), dried over Na2SO4, filtered and concentrated. Purification via flash chromatography with (EtOAc/hexanes: 5% to 80%) afforded the title product (480 mg).

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. washSeparated organic part was washed with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification via flash chromatography with (EtOAc/hexanes: 5% to 80%)

Sources & evidence

ORD record
ord-0a4279da664d4d7da543039b002e628e
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

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