Nitrogen → 6-(2-ethylbutyl)-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One

HRID 897205Notes

Reaction equation

N#N.Br[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9](=[O:14])[CH:8]=[C:7]2[NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH:23]=[CH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:18][CH2:17]1.[Br-].[CH2:32]([CH:34]([CH2:37][CH3:38])[CH2:35][Zn+])[CH3:33]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[Cu]I>[CH2:32]([CH:34]([CH2:37][CH3:38])[CH2:35][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9](=[O:14])[CH:8]=[C:7]2[NH:15][CH:16]1[CH2:17][CH2:18][N:19]([CH2:22][CH:23]=[CH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][CH2:21]1)[CH3:33]

Participants

Conditions

Temperature: 160 °C

Procedure

Into a dry microwave vial under N2 was added 6-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-one (20 mg, 0.046 mmol), Pd(dppf)Cl2 (about 5 mol %), and CuI (about 6 mol %) in dry THF (0.5 mL) followed by 2-ethylbutyl zinc bromide (0.273 mL, 0.138 mmol (0.5M in THF)) dropwise. The solution was heated in the microwave for 10 minutes at 160° C., filtered, and was purified by Prep HPLC to give 4.7 mg (18%) of the desired compound as the TFA salt. MS (ESI(+)Q1MS m/z 445 (M+H)+; 1H NMR (300 MHz, MeOH) δ ppm 0.90 (t, 6H), 1.29-1.38 (m, 4H), 1.60 m, 1H), 1.99 (m, 2H), 2.39 (br d, 2H), 2.60 (m, 2H), 3.24 (br t, 2H), 3.72 (br d, 2H), 3.97 (m, 3H), 5.42 (s, 1H), 6.31-6.40 (m, 1H), 6.95 (d, 1H), 7.24-7.54 (m. 8H), 7.84 (d, 1H).

Workup

filtrationfiltered
customwas purified by Prep HPLC

Sources & evidence

ORD record: ord-4eb11f8e6cdb4ea9961f5aa26870f1cc
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921821B2

Reaction notes

Loading…