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

HRID 1939596Notes

Reaction equation

HRID 1939596 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.Br[C:25]1[CH:26]=[C:27]([C:30]#[N:31])[S:28][CH:29]=1>>[C:30]([C:27]1[S:28][CH:29]=[C:25]([C:14]2[CH:13]=[C:12]3[C:17](=[CH:16][CH:15]=2)[NH:8][C:9]([CH3:22])([CH3:23])[CH:10]=[C:11]3[CH3:21])[CH:26]=1)#[N:31]

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 104464024-(2,2,4-Trimethyl-1,2-dihydroquinolin-6-yl)thiophene-2-carbonitrileYield 91%

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), 5.37 (s, 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-d487bb1a11fd4193bf04cdf0b63f7e99
Source dataset
uspto-grants-1997_12
Patent number
US05696133

Reaction notes

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