Potassium Carbonate → HCID 68455280, compound

HRID 2357564Notes

Reaction equation

HRID 2357564 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](Cl)=[N:7][N:6]=[CH:5]2.[C@H:13]12[CH2:19][C@H:16]([NH:17][CH2:18]1)[CH2:15][N:14]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:17]1[CH2:18][CH:13]3[CH2:19][CH:16]1[CH2:15][N:14]3[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[N:7][N:6]=[CH:5]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 220304246-Bromo-1-chlorophthalazine

Product 1

HCID 68455280HCID 68455280, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 6-bromo-1-chlorophthalazine (Example 1, 0.245 g, 1 mmol), (s,s) tert-butyl 2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylate (0.22 g, 1.1 mmol) and potassium carbonate (0.14 g, 1 mmol) in 5 mL acetonitrile was added to a glass microwave reaction vessel. The reaction mixture was stirred and heated in a Smith Synthesizer® microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 180° C. for 20 min. After about 20 min., all starting material was converted to product (M+1=405, 407). The mixture was concentrated under vacuum, and purified via flash chromatography (silica gel) eluting with 1:1 hexane/ethyl acetate to give (0.18 g) tert-butyl 5-(6-bromophthalazin-1-yl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylate as a yellow solid. Found MS (ES+): 405, 407(M+H)+.

Workup

  1. additionwas added to a glass microwave reaction vessel
  2. concentrationThe mixture was concentrated under vacuum
  3. custompurified via flash chromatography (silica gel)
  4. washeluting with 1:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-18595683100c469fbab62aaf30beb853
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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