Tributylphosphine → HCID 67565487, compound

HRID 1604555Notes

Reaction equation

HRID 1604555 reaction equation
[Br:1][CH2:2][C:3]([NH:5][CH2:6][C:7]([N:9]([C:11]1[C:12]([Cl:31])=[C:13]([C:27]([Cl:30])=[CH:28][CH:29]=1)[CH2:14][O:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[C:23]([CH3:26])[CH:22]=[CH:21]2)[CH3:10])=[O:8])=[O:4].[CH2:32]([P:36]([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH3:35]>O1CCCC1>[Br-:1].[CH2:41]([P+:36]([CH2:32][CH2:33][CH2:34][CH3:35])([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:2][C:3]([NH:5][CH2:6][C:7]([N:9]([C:11]1[C:12]([Cl:31])=[C:13]([C:27]([Cl:30])=[CH:28][CH:29]=1)[CH2:14][O:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[C:23]([CH3:26])[CH:22]=[CH:21]2)[CH3:10])=[O:8])=[O:4])[CH2:42][CH2:43][CH3:44]

Participants

4

Reactant 2

HCID 13831TributylphosphineHCID 19603254HCID 19603254, compound

Product 1

HCID 67565487HCID 67565487, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8-[3-[N-(bromoacetylglycyl)-N-methylamino)-2,6-dichlorobenzyloxy]-2-methylquinoline (200 mg) and tri-n-butylphosphine (140 μl) in tetrahydrofuran (4 ml) was stirred for 2 hours at ambient temperature. The mixture was concentrated, and the residue was purified by flash chromatography (dichloromethane - methanol) to give 8-[3-[N-[2-(tri-n-butylphosphonio)acetylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methylquinoline bromide (128 mg) as an amorphous powder.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by flash chromatography (dichloromethane - methanol)

Sources & evidence

ORD record
ord-d0db1f70f2dc4deba76de69bc4ae765a
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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