Potassium Phosphate, Tribasic → Isobutyl 1-(3-(2-hydroxyphenyl)isoquinolin-1-yl)piperidin-4-ylcarbamate

HRID 386489Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:21])[O-:20])[CH2:14][CH2:13]2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.CC1(C)C(C)(C)OB([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[OH:36])O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:46][C:47]1(C)[C:73]2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=C[C:48]1=2>CC([O-])=O.CC([O-])=O.[Pd+2].O.C1(C)C=CC=CC=1>[OH:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:21])[O:20][CH2:46][CH:47]([CH3:73])[CH3:48])[CH2:14][CH2:13]2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 1-(3-chloroisoquinolin-1-yl)piperidin-4-ylcarbamate (99 mg, 0.27 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenol (92 mg, 0.42 mmol), K3PO4 (0.17 g, 0.80 mmol), Pd(OAc)2 (3.9 mg, 17 μmol), Xantphos (6.6 mg, 11 μmol), toluene (1.3 mL), and water (0.1 mL) was sealed in a microwave vessel and heated by microwave irradiation at 150° C. for 10 minutes. The reaction was filtered and purified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)) to yield isobutyl 1-(3-(2-hydroxyphenyl)isoquinolin-1-yl)piperidin-4-ylcarbamate. LC/MS: m/z 420.2 (M+H)+ at 3.79 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

customwas sealed in a microwave vessel
filtrationThe reaction was filtered
custompurified by reverse phase HPLC (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

Sources & evidence

ORD record: ord-cddce82c4ce649b0bc18fb1f3c0266e0
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372843B2

Reaction notes

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