4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → Tert-butyl 4-(4-aminophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 2367768Notes

Reaction equation

HRID 2367768 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)O1.[C:17]([O:21][C:22]([N:24]1[CH2:29][CH:28]=[C:27](OS(C(F)(F)F)(=O)=O)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>>[C:17]([O:21][C:22]([N:24]1[CH2:25][CH:26]=[C:27]([C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=2)[CH2:28][CH2:29]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

3

Reactant 2

HCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 53415310Tert-butyl 4-(4-aminophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Procedure

The title compound was prepared by Suzuki coupling of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine with 4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (Synthesis, 993, (1991)) according to the procedure in Example 35, step (b). Mass spectrum (ESI, m/z): Calcd. for C16H22N2O2, 275.2 (M+H). found 275.1.

Sources & evidence

ORD record
ord-18e1fbfdad0f47aa8edceb9659f6a873
Source dataset
uspto-grants-2014_04
Patent number
US08697716B2

Reaction notes

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