Triphenylphosphine → 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-iodo-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1858091Notes

Reaction equation

HRID 1858091 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:21])=[C:7]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[I:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:54]([O:58][C:59]([N:61]1[CH2:66][CH2:65][CH2:64][CH2:63][CH:62]1[CH2:67][CH2:68]O)=[O:60])([CH3:57])([CH3:56])[CH3:55]>>[C:54]([O:58][C:59]([N:61]1[CH2:66][CH2:65][CH2:64][CH2:63][CH:62]1[CH2:67][CH2:68][O:21][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[C:3]([I:22])[CH:4]=2)[NH:9][C:8](=[O:12])[C:7]=1[C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=1)=[O:60])([CH3:57])([CH3:56])[CH3:55]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5103438Tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylateHCID 547112397-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-iodoquinolin-2(1H)-one

Product 1

HCID 539972552-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-iodo-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Procedure

To a solution of 2-(2-hydroxyethyl)-piperidine-1-carboxylic acid tert-butyl ester (10 g in 450 mL dry tetrahydrofuran) was added 22.3 g of 7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-iodo-1H-quinolin-2-one followed by 13.7 g of triphenylphosphine and the mixture stirred at room temperature. To this was added 8.2 mL of diethyl azodicarboxylate (DEAD) and stirring was continued for 72 hours. At this time the solvents were removed to a minimum volume in vacuo and the mixture filterd through a silica gel pad to remove the phosphine by-products. The filtrate was concentrated in vacuo to provide the partially purified title compound (17.5 g).

Workup

  1. stirringstirring
  2. customAt this time the solvents were removed to a minimum volume in vacuo
  3. customthe mixture filterd through a silica gel pad to remove the phosphine by-products
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto provide the
  6. custompartially purified title compound (17.5 g)

Sources & evidence

ORD record
ord-5aa8b5cb464744a6ba22fd071d6ab68c
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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