Acetyl chloride → (S)-1-(6-bromo-5-cyclobutoxy-7,8-difluoro-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone

HRID 1051584Notes

Reaction equation

HRID 1051584 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Br:5][C:6]1[C:7]([O:19][CH:20]2[CH2:23][CH2:22][CH2:21]2)=[C:8]2[C:13](=[C:14]([F:17])[C:15]=1[F:16])[NH:12][C@@H:11]([CH3:18])[CH2:10][CH2:9]2>ClCCl.N1C=CC=CC=1>[Br:5][C:6]1[C:7]([O:19][CH:20]2[CH2:21][CH2:22][CH2:23]2)=[C:8]2[C:13](=[C:14]([F:17])[C:15]=1[F:16])[N:12]([C:1](=[O:3])[CH3:2])[C@@H:11]([CH3:18])[CH2:10][CH2:9]2

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 118076083(S)-6-bromo-5-cyclobutoxy-7,8-difluoro-2-methyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 118086274(S)-1-(6-bromo-5-cyclobutoxy-7,8-difluoro-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanoneYield 105.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

Acetyl chloride (0.21 mL, 3.02 mmol) was added dropwise to a 0° C. solution of (S)-6-bromo-5-cyclobutoxy-7,8-difluoro-2-methyl-1,2,3,4-tetrahydroquinoline (1.0 g, 3.02 mmol) in dichloromethane (20 mL) and pyridine (0.6 mL), and the resulting solution was allowed to stir and warm to room temperature overnight. The reaction mixture was diluted with dichloromethane (40 mL), washed with 1 N hydrochloric acid (40 mL) and brine (40 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to afford (S)-1-(6-bromo-5-cyclobutoxy-7,8-difluoro-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone (1.19 g, 99%) as yellow oil. MS (ESI, pos. ion) m/z 374, 376 [M+H]+.

Workup

  1. washwashed with 1 N hydrochloric acid (40 mL) and brine (40 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b79df94b0bc740fa91c134d81486f66d
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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