Acetonitrile → Isobutyl 4-(2-(2-hydroxyphenyl)pyridin-4-yl)piperazine-1-carboxylate

HRID 2245231Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])O1.Cl[C:18]1[CH:23]=[C:22]([N:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][CH:34]([CH3:36])[CH3:35])=[O:31])[CH2:26][CH2:25]2)[CH:21]=[CH:20][N:19]=1.C([O-])([O-])=O.[K+].[K+].CC#N>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.O>[OH:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:18]1[CH:23]=[C:22]([N:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][CH:34]([CH3:36])[CH3:35])=[O:31])[CH2:26][CH2:25]2)[CH:21]=[CH:20][N:19]=1

Participants

Conditions

Temperature: 120 °C

Procedure

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol (25/μL, 120 μmol), 3a (30 mg, 100 μmol), Pd(Ph3P)4 (12 mg, 10 μmol), K2CO3 (28 mg, 200 μmol), CH3CN (900 μL), and H2O (100 μL) were sealed in a microwave vessel and heated by microwave irradiation at 120° C. for 15 minutes. The reaction was filtered and purified by reverse phase HPLC to give compound 1. (10%-99% CH3CN/H2O), (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA). LCMS: m/z 356.1 (M+H)+ at 2.24 minutes (10%-99% CH3CN/H2O), (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA).

Workup

filtrationThe reaction was filtered
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-f70556166651423a8db3cdd77edd78e8
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07683065B2

Reaction notes

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