Sodium Iodide → 8-Benzyloxy-5-((R)-1-(tert-butyldimethylsilanyloxy)-2-{2-[4-(3-chlorophenoxy)phenyl]ethylamino}ethyl)-1H-quinolin-2-one

HRID 2250407Notes

Reaction equation

HRID 2250407 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][NH2:14])=[CH:8][CH:7]=1.[CH2:18]([O:25][C:26]1[CH:27]=[CH:28][C:29]([C@@H:37]([O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42])[CH2:38]Br)=[C:30]2[C:35]=1[NH:34][C:33](=[O:36])[CH:32]=[CH:31]2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.ClCCl>[CH2:18]([O:25][C:26]1[CH:27]=[CH:28][C:29]([C@@H:37]([O:40][Si:41]([C:44]([CH3:45])([CH3:47])[CH3:46])([CH3:43])[CH3:42])[CH2:38][NH:14][CH2:13][CH2:12][C:9]2[CH:10]=[CH:11][C:6]([O:5][C:4]3[CH:15]=[CH:16][CH:17]=[C:2]([Cl:1])[CH:3]=3)=[CH:7][CH:8]=2)=[C:30]2[C:35]=1[NH:34][C:33](=[O:36])[CH:32]=[CH:31]2)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 15606253(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-oneHCID 218318112-[4-(3-Chlorophenoxy)phenyl]ethylamine

Product 1

HCID 685386178-Benzyloxy-5-((R)-1-(tert-butyldimethylsilanyloxy)-2-{2-[4-(3-chlorophenoxy)phenyl]ethylamino}ethyl)-1H-quinolin-2-oneYield 55.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A slurry of the product of step (b) (1.39 g), 8-(benzyloxy)-5-[(R)-2-bromo-1-(tert-butyldimethylsilanyloxy)ethyl]-1H-quinolin-2-one (2.49 g), sodium iodide (1.14 g) and potassium carbonate (2.11 g) in DMSO (7 mL) was heated at 90° C. for 5 h. The solution was allowed to cool, diluted with dichloromethane (60 mL) and washed with water (4×30 mL) then brine (40 mL). The organics were dried over sodium sulfate, concentrated in vacuo and the residue purified by reverse phase HPLC to afford the title intermediate (1.85 g) as a clear oil. m/z: [M+H+] calcd for C38H43ClN2O4Si 655.3. found 655.5.

Workup

  1. temperatureto cool
  2. washwashed with water (4×30 mL)
  3. dry with materialThe organics were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by reverse phase HPLC

Sources & evidence

ORD record
ord-0904e79cbbbb4c519586888729bf2961
Source dataset
uspto-grants-2008_01
Patent number
US07317023B2

Reaction notes

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