1,2-Dimethoxyethane → N-(4-Fluorophenyl)-1-(2-methyl-4-(methylsulfonyl)phenyl)phthalazin-6-amine

HRID 454864Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)=[CH:9][CH:10]=2)[CH:5]=[N:4][N:3]=1.CC1(C)C(C)(C)OB([C:28]2[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][C:29]=2[CH3:38])O1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C([O-])(O)=O.[Na+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.CCO>[F:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[C:2]([C:28]2[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:35])=[O:36])=[CH:30][C:29]=2[CH3:38])=[N:3][N:4]=[CH:5]3)=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 1-chloro-N-(4-fluorophenyl)phthalazin-6-amine (200 mg, 0.73 mmol), 4,4,5,5-tetramethyl-2-(2-methyl-4-(methylsulfonyl)phenyl)-1,3,2-dioxaborolane (260 mg, 0.88 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (26 mg, 0.037 mmol), and sodium carbonate (232 mg, 2.19 mmol) in a 7:2:3 mixture of DME, EtOH and water (3 mL) was heated at 140° C. for 10 min in the Emrys Optimizer® microwave. After cooling to RT, the mixture was diluted with saturated aqueous solution of NaHCO3 and extracted with CH2Cl2 (3×). The combined organics were dried over Na2SO4, filtered and concentrated. The residue was purified using column chromatography (0-75% acetone in hexanes) to yield the title compound as a tan crystalline solid. MS (ESI, pos. ion) m/z: 408.1 (M+1).

Workup

temperatureAfter cooling to RT
extractionextracted with CH2Cl2 (3×)
dry with materialThe combined organics were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified

Sources & evidence

ORD record: ord-43d894c80651461a85ba887bd540812c
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497269B2

Reaction notes

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