tert-Butyl methyl ether → HCID 87158437, compound

HRID 2206930Notes

Reaction equation

HRID 2206930 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:15]([F:18])([F:17])[F:16])[CH2:14][CH2:13][NH:12][CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].F[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:21]=1.C(N(CC)C(C)C)(C)C.COC(C)(C)C>CN(C)C(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:15]([F:18])([F:17])[F:16])[CH2:14][CH2:13][N:12]([C:20]3[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([C:28]([F:29])([F:31])[F:30])[CH:21]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8]

Participants

6

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 81531DiisopropylethylamineHCID 6050854-Fluoro-2-(trifluoromethyl)benzonitrileHCID 87158563HCID 87158563, compound

Product 1

HCID 87158437HCID 87158437, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

3-(3,5-Dichloro-4-fluorophenyl)-3-(trifluoromethyl)pyrrolidine (0.9 g) and 4-fluoro-2-(tri-fluoromethyl)benzonitrile (0.62 g) were weighed, dissolved in N,N-dimethylacetamide (10 ml), added with N,N-diisopropylethylamine (1.0 ml) at room temperature and reacted for 1 hour using a microwave reactor (trade name: INITIATOR™, manufactured by Biotage). The reaction solution was diluted by adding t-butyl methyl ether, and the organic layer was washed three times with water and then saturated brine in that order. The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure and the residue obtained was purified by column chromatography to obtain 4-[3-(3,5-dichloro-4-fluorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile (1.1 g).

Workup

  1. customreacted for 1 hour
  2. additionThe reaction solution was diluted
  3. washthe organic layer was washed three times with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customthe residue obtained
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-20b371f2e3074d888758bcea347670a2
Source dataset
uspto-grants-2016_06
Patent number
US09375000B2

Reaction notes

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