Potassium Carbonate → 6-bromo-1-(octahydroisoquinolin-2(1H)-yl)phthalazine

HRID 2357581Notes

Reaction equation

HRID 2357581 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.[CH2:13]1[CH:22]2[CH:17]([CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:16][CH2:15][NH:14]1.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:14]1[CH2:15][CH2:16][CH:17]3[CH:22]([CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:13]1)=[N:7][N:6]=[CH:5]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 97812DecahydroisoquinolineHCID 220304246-Bromo-1-chlorophthalazine

Product 1

HCID 684525966-bromo-1-(octahydroisoquinolin-2(1H)-yl)phthalazineYield 105.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 6-bromo-1-chlorophthalazine (Example 1, 0.1 g, 411 μmol), decahydroisoquinoline (114 mg, 821 μmol), potassium carbonate (57 mg, 411 μmol) and 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. The mixture was concentrated under vacuum and purified via flash chromatography (silica gel) eluting with a gradient of 2% 2 M ammonia in MeOH/DCM to 6% 2M ammonia in MeOH/DCM to give 6-bromo-1-(octahydroisoquinolin-2(1H)-yl)phthalazine (0.15g) as a yellow solid. Found MS (ES+): 346, 348(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 a gradient of 2% 2 M ammonia in MeOH/DCM to 6% 2M ammonia in MeOH/DCM

Sources & evidence

ORD record
ord-985363a2148c4be6ab99e780fefbc2fd
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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