Sodium Carbonate → (R)-(4-(4-(4-(hydroxymethyl)phenyl)phthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanone

HRID 1689977Notes

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]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:19])[CH2:14][C@H:13]2[CH3:26])=[N:4][N:3]=1.[OH:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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]>[OH:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[O:19])[CH2:14][C@H:13]3[CH3:26])=[N:4][N:3]=2)=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 100 °C

Procedure

(R)-(4-(4-chlorophthalazin-1-yl)-3-methylpiperazin-1-yl)(phenyl)methanone (JK-5) (150 mg, 0.409 mmol), 4-(hydroxymethyl)phenylboronic acid (93.2 mg, 0.613 mmol), and tetrakis(triphenylphosphine)palladium (0) (23.6 mg, 0.023 mmol) were dissolved in toluene (4 mL) and aqueous sodium carbonate (2.0 M, 0.400 mL) under an atmosphere of argon. The reaction was heated at 100° C. for 15 hours, then cooled and taken up in ethyl acetate (80 mL). After washing with aqueous K2CO3 (10%), water, and then saturated sodium chloride, the organics were dried (MgSO4) and evaporated to give a yellow oil. Chromatography over silica gel with a gradient of hexanes/0-100% ethyl acetate gave a pale yellow solid, JK-28. MS (M+H)+=439.2.

Workup

temperaturecooled
washAfter washing with aqueous K2CO3 (10%), water
dry with materialsaturated sodium chloride, the organics were dried (MgSO4)
customevaporated
customto give a yellow oil

Sources & evidence

ORD record: ord-59a1d2b6fb274c0f86947e9b9e782a42
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153633B2

Reaction notes

Loading…