Cyanogen Bromide → HCID 86711207, compound

HRID 1850789Notes

Reaction equation

HRID 1850789 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:17]=[CH:16][C:3]=1[O:4][CH2:5][CH2:6][C@@H:7]1[CH2:9][C@@H:8]1[CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].[N:30]#[C:31]Br>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:19]=[C:18]([S:20]([CH3:23])(=[O:21])=[O:22])[CH:17]=[CH:16][C:3]=1[O:4][CH2:5][CH2:6][C@@H:7]1[CH2:9][C@@H:8]1[CH:10]1[CH2:11][CH2:12][N:13]([C:31]#[N:30])[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 867112054-((1R,2S)-2-{2-{2-fluoro-4-(methylsulfonyl)phenoxy]ethyl}cyclopropyl)piperidine

Product 1

HCID 86711207HCID 86711207, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-((1R,2S)-2-{2-{2-fluoro-4-(methylsulfonyl)phenoxy]ethyl}cyclopropyl)piperidine (Step C, Example 111; 150 mg, 0.428 mmol) and potassium carbonate (244 mg, 1.77 mmol) were stirred in chloroform (7 mL). Cyanogen bromide (61 mg, 0.58 mmol) was added. The mixture was stirred at RT for 15 min and refluxed overnight. The mixture was cooled to RT, mixed with silica gel (5 g), and concentrated to dryness under reduced pressure. The residue was loaded on a silica gel column (15 g of silica gel) and eluted with dichloromethane/methanol (97.5:2.5, 1 L to provide the title compound as an white solid. MS (Multimode) m/z 367 [M+H]+.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe mixture was cooled to RT
  3. additionmixed with silica gel (5 g)
  4. concentrationconcentrated to dryness under reduced pressure
  5. washeluted with dichloromethane/methanol (97.5:2.5, 1 L

Sources & evidence

ORD record
ord-7a63193e604d46cb8b95391c997fd4a7
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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