1,4-Dibromobutane → HCID 131733923, compound

HRID 709833Notes

Reaction equation

HRID 709833 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:25][CH2:26][C:27]#[N:28])[C:13]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=2[F:24])=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[CH2:30][CH2:31][CH2:32][CH2:33]Br.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl-].[NH4+]>C1COCC1>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:25][C:26]2([C:27]#[N:28])[CH2:33][CH2:32][CH2:31][CH2:30]2)[C:13]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=2[F:24])=[N:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 80561,4-DibromobutaneHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 131733922HCID 131733922, compound

Product 1

HCID 131733923HCID 131733923, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(5-(((tert-butyl(dimethyl)silyl)oxy)methyl)-2-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)propanenitrile (514 mg) and 1,4-dibromobutane (0.30 mL) in THF (10 mL) was added a THF solution (1 M, 3.9 mL) of lithium bis(trimethylsilyl)amide, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (514 mg) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2b5a9f2b72a74fcbaa2bbb6385773498
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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