Toluene → HCID 57581514, compound

HRID 1689956Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:14]([CH3:25])[CH2:13]2)=[N:4][N:3]=1.[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:25][C@H:14]1[CH2:13][N:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:3][N:4]=2)[CH2:17][CH2:16][N:15]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

Participants

Conditions

Temperature: 100 °C

Procedure

(S)-tert-butyl 4-(4-chlorophthalazin-1-yl)-2-methylpiperazine-1-carboxylate (2.10 g, 5.79 mmol), phenylboronic acid (1.06 g, 8.69 mmol), and tetrakis(triphenylphosphine)palladium (0) (0.334 g, 0.289 mmol) were placed in a flask under argon. Degassed toluene (50 mL) and aqueous sodium carbonate (2.0 M, 5.0 mL) were added and the reaction heated at 100° C. for 16 hours. The reaction was allowed to cool, diluted with 150 mL of ethyl acetate, and then washed with aqueous K2CO3 (10%), and saturated sodium chloride. The dried organics (MgSO4) were evaporated to give yellow oil. Chromatography over silica gel with a gradient of hexanes/0-40% ethyl acetate gave an off-white solid. MS (M+H)+=405.2.

Workup

temperatureto cool
washwashed with aqueous K2CO3 (10%), and saturated sodium chloride
customThe dried organics (MgSO4) were evaporated
customto give yellow oil

Sources & evidence

ORD record: ord-e8c285c8dfd241cda357b48d62036b7b
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153633B2

Reaction notes

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