Potassium Carbonate → HCID 68455205, compound

HRID 2357565Notes

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[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[N:7][N:6]=[CH:5]2.[CH:26]1([NH:29][C:30](=[O:47])[C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[C:33](B3OC(C)(C)C(C)(C)O3)[CH:32]=2)[CH2:28][CH2:27]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:26]1([NH:29][C:30]([C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[C:33]([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[C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])=[N:7][N:6]=[CH:5]4)[CH:32]=2)=[O:47])[CH2:27][CH2:28]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of tert-butyl 5-(6-bromophthalazin-1-yl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylate (0.18 g, 0.44 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.14g, 0.44 mmol), tetrakis(triphenylphosphine)palladium (25 mg, 0.022 mmol) and 2 M potassium carbonate (0.66 mL, 1.32 mmol) in 5 mL DME/EtOH (4:1) was stirred at 90° C. for 2 h. The mixture was transferred directly to a column and purified via flash chromatography (silica gel) eluting with a gradient of 2% 2 M ammonia in MeOH/DCM to 10% 2M ammonia in MeOH/DCM to give tert-butyl 5-(6-(5-(cyclopropylcarbamoyl)-2-methylphenyl) phthalazin-1-yl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylate (0.20 g) as a yellow solid.

Workup

custompurified via flash chromatography (silica gel)
washeluting with a gradient of 2% 2 M ammonia in MeOH/DCM to 10% 2M ammonia in MeOH/DCM

Sources & evidence

ORD record: ord-1e95d3fae8944f1ba006efde23805c16
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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