Cyanogen Bromide → HCID 178511844, compound

HRID 1742739Notes

Reaction equation

HRID 1742739 reaction equation
[N:1]#CBr.[F:4][C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH:14]3[CH2:20][CH:19]4[N:21]([CH3:22])[CH:16]([CH2:17][CH2:18]4)[CH2:15]3)=[N:10][NH:11]2)=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[C:22]([N:21]1[CH:19]2[CH2:18][CH2:17][CH:16]1[CH2:15][CH:14]([C:9]1[C:8]3[C:12](=[CH:13][C:5]([F:4])=[CH:6][CH:7]=3)[NH:11][N:10]=1)[CH2:20]2)#[N:1]

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 178479849HCID 178479849, compound

Product 1

HCID 178511844HCID 178511844, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Cyanogen bromide (2.75 g) was added in one portion to a suspension of 3-(6-fluoro-1H-indazol-3-yl)-8-methyl-8-azabicyclo[3.2.1]octane (4.90 g) and potassium carbonate (2.75 g) in 70 ml of THF at room temperature. The mixture was stirred for 2 hours, then diluted with water and the product was extracted into ethyl acetate. The organic solution was washed with brine, dried over MgSO4, filtered and concentrated to leave 3.4 g of crude solids. The solids were purified by flash chromatography over silica gel and recrystallized from ethanol to yield 1.15 g of the desired product, m.p. 182°-184° C.

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. washThe organic solution was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto leave 3.4 g of crude solids
  7. customThe solids were purified by flash chromatography over silica gel
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-39146583e1e74afd982b417630e42817
Source dataset
uspto-grants-1994_08
Patent number
US05340936

Reaction notes

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