Sodium Iodide → HCID 57989313, compound

HRID 471288Notes

Reaction equation

HRID 471288 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:21]Br)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:31][C:32]([CH3:43])([CH3:42])[CH2:33][C:34]1[CH:35]=[C:36]([CH2:40][OH:41])[CH:37]=[CH:38][CH:39]=1.[I-].[Na+].CCN(C(C)C)C(C)C>C(#N)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:21][NH:31][C:32]([CH3:43])([CH3:42])[CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][OH:41])[CH:35]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531Diisopropylethylamine2×HCID 15606253(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-oneHCID 57989118HCID 57989118, compound2×

Product 1

HCID 57989313HCID 57989313, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (R)-8-(benzyloxy)-5-(2-bromo-1-(tert-butyldimethylsilyloxy)ethyl)quinolin-2 (1H)-one (0.518 g) and (3-(2-amino-2-methylpropyl)phenyl)methanol (0.19 g) (example 275, step c) and sodium iodide (0.159 g) and Hunig's Base (0.555 mL) in acetonitrile (3 mL) was heated at reflux under nitrogen for 2 days. Further (3-(2-amino-2-methylpropyl)phenyl)methanol (0.19 g) and Hunig's Base (0.185 mL) were added and heating at reflux continued for 1 day. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and brine, the organic layer was dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography eluting with 3% methanol and 1% triethylamine in dichloromethane. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.44 g.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 2 days
  3. temperatureheating
  4. temperatureat reflux
  5. custompartitioned between ethyl acetate and brine
  6. dry with materialthe organic layer was dried over sodium sulphate
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure
  9. customThe crude product was purified by flash silica chromatography
  10. washeluting with 3% methanol and 1% triethylamine in dichloromethane
  11. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-af77ec3746714833a602ccbf84d53b4a
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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