Nitrogen → HCID 73712337, compound

HRID 897206Notes

Reaction equation

HRID 897206 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-].[CH3:32][CH:33]([CH3:36])[CH2:34][Zn+]>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>[CH3:32][CH:33]([CH3:36])[CH2:34][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

Participants

7

Reactant 3

HCID 947NitrogenHCID 737123526-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-OneHCID 178448254HCID 178448254, compound

Product 1

HCID 73712337HCID 73712337, compoundYield 18.8%

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 N2 was added 6-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-one (20 mg, 0.046 mmol), Pd(dppf)Cl2 (˜5 mol %), and CuI (˜6 mol %) in dry THF (0.5 mL) followed by 2-methylpropyl 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 3.6 mg (15%) of the desired compound as the TFA salt. MS (ESI(+)Q1MS m/z 417 (M+H)+; 1H NMR (300 MHz, MeOH) δ ppm 0.93 (d, 6H), 1.91-2.03 (m, 3H), 2.41 (br d, 2H), 2.58 (d, 2H), 3.23 (br t, 2H), 3.72 (br d, 2H), 3.96 (m, 3H), 5.42 (s, 1H), 6.29-6.40 (m, 1H), 6.95 (d, 1H), 7.24-7.54 (m. 8H), 7.83 (d, 1H).

Workup

  1. filtrationfiltered
  2. customwas purified by Prep HPLC

Sources & evidence

ORD record
ord-52fce34d521a40a5a3c995b6296167a6
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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