Triethylamine → HCID 131735155, compound

HRID 931103Notes

Reaction equation

HRID 931103 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:18]([Si:22]([CH3:32])([CH3:31])S(OC(F)(F)F)(=O)=O)([CH3:21])([CH3:20])[CH3:19]>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([C:8]([O:10][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:32])[CH3:31])=[CH2:9])[N:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 112985782-Acetyl-6-bromopyridineHCID 102042439HCID 102042439, compound

Product 1

HCID 131735155HCID 131735155, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(6-bromopyridin-2-yl)ethanone (1000 mg, 5.0 mmol) and triethylamine (2.1 mL, 15.0 mmol) at 0° C. in dichloromethane (14 mL) was added trifluoromethyl tert-butyldimethylsilanesulfonate (1.4 mL, 6.2 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, and concentrated. The residue was purified via flash chromatography (0-30% ethyl acetate in heptanes) to afford 2-bromo-6-(1-((tert-butyldimethylsilyl)oxy)vinyl)pyridine as a colorless oil (1450 mg, 92%). 1H NMR (400 MHz, DMSO-d6) δ 0.22 (s, 6H), 0.98 (s, 9H), 4.62-4.63 (m, 1H), 5.52 (s, 1H), 7.56-7.62 (m, 2H), 7.82 (s, 1H).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified via flash chromatography (0-30% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-3e087a96327a4b05a10af880c741ea7b
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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