6-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One → HCID 73712345, compound

HRID 897203

Reaction equation

HRID 897203 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[C:5]2[NH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH:21]=[CH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:16][CH2:15]1.[Br-].[CH2:30]([Zn+])[CH2:31][CH3:32]>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>[CH2:30]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[C:5]2[NH:13][CH:14]1[CH2:15][CH2:16][N:17]([CH2:20][CH:21]=[CH:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:18][CH2:19]1)[CH2:31][CH3:32]

Participants

6

Reactant 2

HCID 737123526-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-OneHCID 178455869HCID 178455869, compound

Product 1

HCID 73712345HCID 73712345, compoundYield 73.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
160 °C

Procedure

Into a dry microwave vial under nitrogen 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 n-propyl 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 13.6 mg (57%) of the desired compound as the TFA salt. MS (ESI(+)Q1MS m/z 403 (M+H)+; 1H NMR (300 MHz, MeOH) δ ppm 0.96 (t, 3H), 1.70 (m, 2H), 1.98-2.01 (m, 2H), 2.39 (br d, 2H), 2.69 (t, 2H), 3.23 (br t, 2H), 3.72 (m, 2H), 3.88-3.98 (m, 3H), 5.42 (s, 1H), 6.30-6.40 (m, 1H), 6.95 (d, 1H), 7.24-7.54 (m 0.8H), 7.85 (s, 1H).

Workup

  1. filtrationfiltered
  2. customwas purified by Prep HPLC

Sources & evidence

ORD record
ord-990d47ffb18b41ebb7cac08ada974b15
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Linked notes

Loading…