4-Aminophenylboronic acid → HCID 68439640, compound

HRID 1992001Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[C:11]([O:15][C:16]([N:18]1[C@@H:23]([CH3:24])[CH:22]=[C:21](OS(C(F)(F)F)(=O)=O)[CH2:20][C@@H:19]1[CH3:33])=[O:17])([CH3:14])([CH3:13])[CH3:12]>>[C:11]([O:15][C:16]([N:18]1[CH:19]([CH3:33])[CH:20]=[C:21]([C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[CH2:22][CH:23]1[CH3:24])=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

Reactant 2

HCID 27346154-Aminophenylboronic acid

HCID 86606279HCID 86606279, compound

Product 1

HCID 68439640HCID 68439640, compoundYield 57%

Procedure

The title compound was then prepared according to the Suzuki coupling procedure of Example 35, step (b) using 4-aminophenylboronic acid (219 mg, 1.00 mmol) and cis/trans-2,6-dimethyl-4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (as prepared above, 321 mg, 1.00 mmol). Silica gel chromatography (10-20% EtOAc/hexanes) afforded 4-(4-amino-phenyl)-2,6-dimethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (172 mg, 57%): Mass spectrum (ESI, m/z): Calcd. for C18H26N2O2, 303.2 (M+H) found 303.1.

Sources & evidence

ORD record: ord-e1152a0429e3476d87dc43c79017b735
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645755B2

Reaction notes

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