Acetonitrile → HCID 86004847, compound

HRID 1969451Notes

Reaction equation

HRID 1969451 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](O)([CH3:10])[CH3:9])[CH:5]=[CH:4][CH:3]=1.B(F)(F)F.[CH3:16][CH2:17][O:18]CC.[OH-].[Na+].C(#[N:25])C>>[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH:25][C:17](=[O:18])[CH3:16])([CH3:10])[CH3:9])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 227143012-(6-Bromopyridin-2-yl)propan-2-ol

Product 1

HCID 86004847HCID 86004847, compoundYield 26%

Procedure

Dissolve 2-(6-bromo-pyridin-2-yl)-propan-2-ol (10.6 g, 50 mmol) in acetonitrile (40 mL). Add BF3-Et2O (20 mL, 125 mmol) and reflux for 3 days. Cool to room temperature, add ice and neutralize the reaction with 5N NaOH and extract with dichloromethane. Purify over silica (120 g) eluting with 0 to 100% EtOAc:hexanes to give N-[1-(6-bromo-pyridin-2-yl)-1-methyl-ethyl]-acetamide (3.3 g, 26%), MS (m/z): 257 and 259 (M+H)+ and recovered 2-(6-bromo-pyridin-2-yl)-propan-2-ol (3.7 g, 34%).

Workup

  1. additionadd ice
  2. extractionextract with dichloromethane
  3. customPurify over silica (120 g)
  4. washeluting with 0 to 100% EtOAc

Sources & evidence

ORD record
ord-85ea2acb4e7b431e8ab5b1b82e0bc399
Source dataset
uspto-grants-2013_04
Patent number
US08426448B2

Reaction notes

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