1,2-Dimethoxyethane → HCID 68455267, compound

HRID 2357541Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O: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.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.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.C(O)C>[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O: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

Participants

Conditions

Temperature: 90 °C

Procedure

A 10 mL round-bottomed flask under argon was charged with 1-chloro-6-(4-fluorophenoxy)phthalazine (42.90 mg, 0.15 mmol), tetrakis(triphenylphosphine)palladium (9 mg, 0.008 mmol), 2-chlorophenylboronic acid (37 mg, 0.23 mmol), ethylene glycol dimethyl ether (1.6 mL), and ethanol (0.4 mL), followed by 2M aqueous sodium carbonate solution (0.23 mL, 0.45 mmol). The reaction was stirred at 90° C. for 3 h. The cooled reaction mixture was diluted with DCM and washed with saturated aqueous NaHCO3 and brine, then dried (MgSO4). Flash chromatography eluting with a gradient of 25:10:65, 40:10:50, 50:10:40, 60:10:30, and 70:10:20 ethyl acetate-dichloromethane-hexanes gave the title compound as a tan amorphous solid. MS (ES+): 351.1 (M+H)+.

Workup

customThe cooled reaction mixture
washwashed with saturated aqueous NaHCO3 and brine
dry with materialdried (MgSO4)
washFlash chromatography eluting with a gradient of 25:10:65, 40:10:50, 50:10:40, 60:10:30, and 70:10:20 ethyl acetate-dichloromethane-hexanes

Sources & evidence

ORD record: ord-f30fca342be94ff591ba21fd9720e332
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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