Triphenylphosphine → Tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinolin-7-yl]oxy}piperidine-1-carboxylate

HRID 394157Notes

Reaction equation

HRID 394157 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[C:17]([OH:19])[CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][C:13](=[O:28])[N:14]2[C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:27].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O[CH:49]1[CH2:54][CH2:53][N:52]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH2:51][CH2:50]1.N(C(OCC)=O)=NC(OCC)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[C:17]([O:19][CH:49]2[CH2:54][CH2:53][N:52]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH2:51][CH2:50]2)[CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13](=[O:28])[N:14]2[C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:27]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 22648031HCID 22648031, compound2×

Product 1

HCID 22647973Tert-butyl 4-{[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinolin-7-yl]oxy}piperidine-1-carboxylate

Procedure

The title compound was prepared from 55 mg 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-hydroxyquinolin-2(1H)-one (INTERMEDIATE 9), 500 mg of polymer-bound Ph3P, 128 mg of tert-butyl 4-hydroxypiperidine-1-carboxylate, and 122 mg of diethyl azodicarboxylate by a procedure analogous to that described in EXAMPLE 2. Mass spectrum (ESI) 599 (M+1).

Sources & evidence

ORD record
ord-2adf3eba853d43ac9bc1c596bf530419
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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