Isobutyronitrile → 2-(5-Bromopyridin-2-yl)-2-methylpropanenitrile

HRID 1852446Notes

Reaction equation

HRID 1852446 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][CH:10]([CH3:13])[C:11]#[N:12].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[NH4+].[Cl-]>C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]([CH3:13])([CH3:9])[C:11]#[N:12])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 6559IsobutyronitrileHCID 25517Ammonium ChlorideHCID 693532,5-DibromopyridineHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 115866222-(5-Bromopyridin-2-yl)-2-methylpropanenitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2,5-dibromopyridine (5.0 g, 21 mmol) and 2-methylpropanenitrile (1.6 g, 23 mmol) in toluene (50 mL) under nitrogen was added NaHMDS (12 mL, 23 mmol, 2.0M in THF) dropwise at 0° C. The resulting solution was stirred at ambient temperature overnight before the addition of saturated aqueous NH4Cl (20 mL). The resulting mixture was extracted with EtOAc (3×30 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by MPLC on Silica gel (eluting with 1-3% EtOAc/hexane) to afford the title compound as a light yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.65 (s, 1H), 7.85 (d, J=8.7 Hz, 1H), 7.51 (d, J=8.7 Hz, 1H), 1.75 (s, 6H). MS ESI [M+H]+ m/z 225.227.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (3×30 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by MPLC on Silica gel (eluting with 1-3% EtOAc/hexane)

Sources & evidence

ORD record
ord-7700f0e048ce46068c3856c2e1fc90f7
Source dataset
uspto-grants-2015_02
Patent number
US08962608B2

Reaction notes

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