Sodium Iodide → 5-((1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)amino]-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-8-(benzyloxy)quinolin-2(1H)-one

HRID 1925502Notes

Reaction equation

HRID 1925502 reaction equation
[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:20][CH2:21][NH2:22])[CH:17]=[CH:18][CH:19]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:23]([O:30][C:31]1[CH:32]=[CH:33][C:34]([C@@H:42]([O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])[CH2:43]Br)=[C:35]2[C:40]=1[NH:39][C:38](=[O:41])[CH:37]=[CH:36]2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])O.[Na+].[I-].[Na+]>CS(C)=O.O>[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:20][CH2:21][NH:22][CH2:43][C@@H:42]([C:34]4[CH:33]=[CH:32][C:31]([O:30][CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[C:40]5[C:35]=4[CH:36]=[CH:37][C:38](=[O:41])[NH:39]5)[O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])[CH:17]=[CH:18][CH:19]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 15606253(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-oneHCID 67520349(2-{3-[2-(1-Adamantyl)ethoxy]phenyl}ethyl)amine

Product 1

HCID 675208935-((1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)amino]-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-8-(benzyloxy)quinolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of Intermediate 31 (0.51 g, 1.7 mmol) in dimethyl sulfoxide (1.5 mL) and (R)-8-(benzyloxy)-5-(2-bromo-1-(tert-butyldimethylsilyloxy)ethyl)quinolin-2(1H)-one (1.06 g, 2.17 mmol) in dimethyl sulfoxide (2 mL) was added sodium hydrogen carbonate (0.53 g, 6.37 mmol) and sodium iodide (0.970 g, 6.47 mmol). The reaction mixture was stirred at 120° C. for 2 hours. The reaction was poured into water and filtered. The crude was purified by column chromatography with silica gel, eluting by methylen chloride giving the title compound as a solid (0.84 g, 63%). MS (M+): 708.

Workup

  1. filtrationfiltered
  2. customThe crude was purified by column chromatography with silica gel
  3. washeluting by methylen chloride giving the title compound as a solid (0.84 g, 63%)

Sources & evidence

ORD record
ord-6931393a02d04f579a6fd8859e8dce34
Source dataset
uspto-grants-2012_05
Patent number
US08178679B2

Reaction notes

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