Nitrogen → HCID 73712339, compound

HRID 897204Notes

Reaction equation

HRID 897204 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]([CH3:37])[CH2:34][CH2:35][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]([CH3:37])[CH2:34][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[CH2:21][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

Participants

7

Reactant 3

HCID 947NitrogenHCID 737123526-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-OneHCID 178445882HCID 178445882, compound

Product 1

HCID 73712339HCID 73712339, compoundYield 31.3%

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 (about 5 mol %), and CuI (about 6 mol %) in dry THF (0.5 mL) followed by 3-methylbutyl 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 6.2 mg (25%) of the desired compound as the TFA salt. MS (ESI(+)Q1MS m/z 431 (M+H)+; 1H NMR (300 MHz, MeOH) δ ppm 0.97 (d, 6H), 1.52-1.64 (m, 3H), 1.97 (br q, 2H), 2.40 (br d, 2H), 2.72 (br t, 2H), 3.23 (br t, 2H), 3.73 (d, 2H), 3.93-3.97 (m, 3H), 5.42 (s, 1H), 6.30-6.40 (m, 1H), 6.95 (d, 1H), 7.23-7.54 (m. 8H), 7.86 (d, 1H).

Workup

  1. filtrationfiltered
  2. customwas purified by Prep HPLC

Sources & evidence

ORD record
ord-632bb5003a99402881e9cea6b3bc549b
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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