Thionyl Chloride → HCID 86692532, compound

HRID 1748580Notes

Reaction equation

HRID 1748580 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C:11]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([Br:23])=[CH:18][N:17]=2)(O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.O.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH:12]=[C:11]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([Br:23])=[CH:18][N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 86585896Sodium bicarbonate waterHCID 86692531HCID 86692531, compound

Product 1

HCID 86692532HCID 86692532, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-(5-bromo-3-methylpyridin-2-yl)-4-hydroxyazepane-1-carboxylic acid tert-butyl ester (1.90 g) in pyridine (20 ml) was added thionyl chloride (1.47 g) under ice-cooling, and stirred at the same temperature for 1 hour. After completion of the reaction, saturated sodium bicarbonate water was added thereto, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give a mixture (1.02 g) of 4-(5-bromo-3-methylpyridin-2-yl)-2,3,6,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester and 4-(5-bromo-3-methylpyridin-2-yl)-2,3,4,7-tetrahydroazepine-1-carboxylic acid tert-butyl ester as a colorless clear oil.

Workup

  1. temperaturecooling
  2. additionwas added
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-59eb1f5d08814cad91a6514de9a532a1
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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