Cyanogen Bromide → HCID 86711214, compound

HRID 1850799Notes

Reaction equation

HRID 1850799 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][CH2:10][C@@H:11]1[CH2:13][C@@H:12]1[CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+].[N:34]#[C:35]Br>C(Cl)Cl>[C:35]([N:17]1[CH2:16][CH2:15][CH:14]([C@H:12]2[CH2:13][C@H:11]2[CH2:10][CH2:9][O:8][C:7]2[N:6]=[CH:5][C:4]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:3][C:2]=2[CH3:1])[CH2:19][CH2:18]1)#[N:34]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 70856333HCID 70856333, compound

Product 1

HCID 86711214HCID 86711214, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To the solution of tert-butyl (5-methyl-6-{2-[(1S,2R)-2-piperidin-4-ylcyclopropyl]ethoxy}pyridin-3-yl)acetate (770 mg, 2.1 mmol) in 15 mL of DCM was added K2CO3 (3 eq., 852 mg, in 5 mL of water) at room temperature followed by addition of cyanogen bromide (1.2 eq., 0.85 mL of 3M soln in DCM) at room temperature. The mixture was then stirred for 30 min at room temperature and then diluted with 20 mL DCM. The solution was washed with sat'd NaHCO3 aq. soln, separated, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. The residue was purified by ISCO column (40 g silica gel) using ethyl acetate in hexane (0-60%, 700 ml) to give the title compound. LCMS (ESI) m/z 400 [M+H]+.

Workup

  1. washThe solution was washed with sat'd NaHCO3 aq. soln
  2. customseparated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe residue was purified by ISCO column (40 g silica gel)

Sources & evidence

ORD record
ord-f9de1697864240b88435f6c91006778b
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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