Trifluoroacetic acid → HCID 86692460, compound

HRID 1748510Notes

Reaction equation

HRID 1748510 reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2([C:25]#[N:26])[CH2:24][CH2:23][C:18]3(OCC[O:19]3)[CH2:17][CH2:16]2)=[N:13][CH:14]=1>>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2([C:25]#[N:26])[CH2:16][CH2:17][C:18](=[O:19])[CH2:23][CH2:24]2)=[N:13][CH:14]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86692457HCID 86692457, compound

Product 1

HCID 86692460HCID 86692460, compoundYield 94.7%

Procedure

Trifluoroacetic acid (4.1 ml) was added to 8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4,5]decane-8-carbonitrile (3.4 g) described in Reference Example 82 at room temperature, and stirred at the same temperature for 22 hours. After completion of the reaction, the solvent and trifluoroacetic acid were evaporated and the resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 1-(5-bromopyridin-2-yl)-4-oxocyclohexanecarbonitrile (2.78 g) as a white solid.

Workup

  1. customdescribed in Reference Example 82 at room temperature
  2. customAfter completion of the reaction
  3. customthe solvent and trifluoroacetic acid were evaporated
  4. customthe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-abeb5c6f102849b8a73a079526879e11
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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