(1-(tert-Butoxycarbonyl)-2,2,4-trimethyl-1,2-dihydroquinolin-6-yl)boronic acid → 2,2,4-Trimethyl-1,2-dihydroquinoline

HRID 2294508Notes

Reaction equation

HRID 2294508 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][C:14](B(O)O)=[CH:15][CH:16]=2)[C:11]([CH3:21])=[CH:10][C:9]1([CH3:23])[CH3:22])=O)(C)(C)C.BrC1C=C(C#N)SC=1>>[CH3:22][C:9]1([CH3:23])[CH:10]=[C:11]([CH3:21])[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:8]1

Participants

3

Reactant 2

HCID 10615401(1-(tert-Butoxycarbonyl)-2,2,4-trimethyl-1,2-dihydroquinolin-6-yl)boronic acidHCID 142923554-Bromothiophene-2-carbonitrile

Product 1

HCID 89812,2,4-Trimethyl-1,2-dihydroquinolineYield 146.6%

Procedure

This compound was prepared by General Method 2 from compound 9 (200 mg, 0.63 mmol) and 4-bromo-2-cyanothiophene (0.50 g, 2.65 mmol). The crude product was purified by prep. TLC (20×20 cm, 1000 μm, 25% ETOAc:Hexane) to afford 160 mg (91%) of Compound 452 as a yellow oil. Data for Compound 452: Rf 0.50 (silica gel, 25% EtOAc:hex); 1H NMR(400 MHz, CDCl3) 7.79 (s, 1H), 7.46 (s, 1H), 7.20 (s, 1H), 7.16 (d, J=8.3, 1H), 6.46 (d, J=8.3, 1H), 2.03 (s, 3H), 1.31 (s, 6H); IR (film, NaCl) 1159, 1381, 1402, 1449, 1476, 1499, 1609, 1653, 2216, 2915, 3294, 3584.

Workup

  1. customThe crude product was purified by prep

Sources & evidence

ORD record
ord-915bcec655b8470a8ffbfcfc2e1cd9fe
Source dataset
uspto-grants-1997_11
Patent number
US05688810

Reaction notes

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