4-Nitrophenylboronic acid → HCID 22049016, compound

HRID 2367809Notes

Reaction equation

HRID 2367809 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]([O:17][C:18]([N:20]1[CH2:25][CH:24]=[C:23](C2C=CC(N)=CC=2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>CCOC(C)=O>[C:13]([O:17][C:18]([N:20]1[CH2:21][CH:22]=[C:23]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:24][CH2:25]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 27735524-Nitrophenylboronic acidHCID 53415310Tert-butyl 4-(4-aminophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 22049016HCID 22049016, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared by the Suzuki coupling procedure of Example 35, step (b) using 4-nitrophenylboronic acid (167 mg, 1.00 mmol) and 4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (as prepared in Example 13, step (a), 295 mg, 1.00 mmol). Silica gel chromatography (10% EtOAc in hexanes) afforded the title compound (273 mg, 90%) as an oil. 1H-NMR (CDCl3; 400 MHz): δ 8.19 (d, 2H, J=8.8 Hz), 7.50 (d, 2H, J=8.8 Hz), 6.23 (m, 1H), 4.12 (m, 2H), 3.66 (m, 2H), 2.54 (m, 2H), 1.49 (s, 9H).

Workup

  1. customThe title compound was prepared by the Suzuki coupling procedure of Example 35, step (b)

Sources & evidence

ORD record
ord-860780c88d794d5b8a268cc33909b8ed
Source dataset
uspto-grants-2014_04
Patent number
US08697716B2

Reaction notes

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