Triphenylphosphine → 2-{2-[3-(3-Bromophenyl)-7-chloro-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1857615Notes

Reaction equation

HRID 1857615 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:23])[NH:10][C:11]3[C:16]([C:17]=2[OH:18])=[CH:15][C:14]([N+:19]([O-:21])=[O:20])=[C:13]([Cl:22])[CH:12]=3)[CH:5]=[CH:6][CH:7]=1.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]1[CH2:37][CH2:38]O)=[O:30])([CH3:27])([CH3:26])[CH3:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>>[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH:32]1[CH2:37][CH2:38][O:18][C:17]1[C:16]2[C:11](=[CH:12][C:13]([Cl:22])=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=2)[NH:10][C:9](=[O:23])[C:8]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)=[O:30])([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5103438Tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylateHCID 547102463-(3-bromophenyl)-7-chloro-4-hydroxy-6-nitro-1H-quinolin-2-one

Product 1

HCID 543094672-{2-[3-(3-Bromophenyl)-7-chloro-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl esterYield 60%

Procedure

To a solution of 3-(3-bromophenyl)-7-chloro-4-hydroxy-6-nitro-1H-quinolin-2-one (100 mg in 4.0 mL of tetrahydrofuran) at 0° C. was added 64 mg of 2-(2-hydroxyethyl)-piperidine-1-carboxylic acid tert-butyl ester and 93 mg of triphenylphosphine followed by 0.050 mL of diethyl azodicarboxylate and the mixture warmed to room temperature. After 20 hours, the solvents were removed in vacuo and the residue purified by flash chromatography on silica gel (hexane:ethylacetate, 2:1) to give the title compound (92 mg).

Workup

  1. customthe solvents were removed in vacuo
  2. customthe residue purified by flash chromatography on silica gel (hexane:ethylacetate, 2:1)

Sources & evidence

ORD record
ord-d2a52b1c8bfe48ae9cbef74699dec539
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

Loading…