Potassium Carbonate → HCID 68454681, compound

HRID 2357576Notes

Reaction equation

HRID 2357576 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH:16]3[CH2:18][CH:13]1[CH2:14][N:15]3[CH:19]([CH3:21])[CH3:20])=[N:7][N:6]=[CH:5]2.[CH:22]1([NH:25][C:26](=[O:43])[C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[C:29](B3OC(C)(C)C(C)(C)O3)[CH:28]=2)[CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:22]1([NH:25][C:26](=[O:43])[C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[C:8]([N:12]3[CH2:17][CH:16]5[CH2:18][CH:13]3[CH2:14][N:15]5[CH:19]([CH3:21])[CH3:20])=[N:7][N:6]=[CH:5]4)[CH:28]=2)[CH2:23][CH2:24]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 684549782-(6-Bromophthalazin-1-yl)-5-isopropyl-2,5-diaza-bicyclo[2.2.1]heptane

Product 1

HCID 68454681HCID 68454681, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 20074477Dimethoxyethane ethanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(6-bromophthalazin-1-yl)-5-isopropyl-2,5-diaza-bicyclo[2.2.1]heptane (60 mg, 173 μmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (52 mg, 173 μmol) and tetrakis(triphenylphosphine)palladium (10 mg, 9 μmol)in 5 mL DME/EtOH (4:1) was treated with 2M potassium carbonate (0.5 mL, 1 mmol) at 22° C. under nitrogen. The mixture was heated up to 90° C. and stirred for 1 h. The reaction was monitored by MS. After about 1 h at 90° C., MS showed all starting material was converted to product (M+1=442). The mixture was cooled down to room temperature (22° C.). The mixture was transferred directly to silica gel and purified via flash chromatography (silica gel) eluting with a gradient of 2% 2 M ammonia in MeOHIDCM to 6% 2 M ammonia in MeOH/DCM to give the title compound (60 mg). Found MS (ES+): 442(M+H)+.

Workup

  1. waitAfter about 1 h at 90° C.
  2. temperatureThe mixture was cooled down to room temperature (22° C.)
  3. custompurified via flash chromatography (silica gel)
  4. washeluting with a gradient of 2% 2 M ammonia in MeOHIDCM to 6% 2 M ammonia in MeOH/DCM

Sources & evidence

ORD record
ord-08ebbbafcac84e3697d62a3e55f259f4
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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