Trimethylsilyl iodide → HCID 52949494, compound

HRID 2194904Notes

Reaction equation

HRID 2194904 reaction equation
C(OC(=O)[NH:7][CH2:8][CH:9]([C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[CH2:42][CH2:43][C:44]#[N:45])=[CH:32][C:31]=1[CH3:46])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][C:21]2[C:26]([Cl:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=2[Cl:29])=[CH:13][CH:12]=1)(C)(C)C.I[Si](C)(C)C>C(#N)C.C([O-])(O)=O.[Na+]>[NH2:7][CH2:8][CH:9]([C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[CH2:42][CH2:43][C:44]#[N:45])=[CH:32][C:31]=1[CH3:46])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][O:20][C:21]2[C:26]([Cl:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=2[Cl:29])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 131730112HCID 131730112, compound

Product 1

HCID 52949494HCID 52949494, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of tert-butyl(2-[2′42-cyanoethyl)-3-methylbiphenyl-4-yl]-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}propyl)carbamate from step 1 (1 eq.) in acetonitrile (0.05M) at room temperature was added iodo trimethylsilane (2 eq.). The reaction mixture was stirred for 10 min at room temperature poured in saturated aqueous NaHCO3 and extracted with EtOAc. The organic extract was washed with brine, dried over Na2SO4, filtered and concentrated. Purification by column chromatography on silica gel, eluting with CH2Cl2/MeOH(NH3 2M) 4%, afforded the title compound as a foam. 1H NMR (500 MHz, CDCl3): δ 7.38-7.25 (m, 5H), 7.16 (dd, 1H), 7.13 (s, 2H), 7.03 (d, 1H), 6.98 (d, 2H), 6.84 (d, 2H), 4.38-4.32 (m, 4H), 3.34-3.30 (m, 1H), 3.10-2.94 (m, 3H), 3.01 (t, 2H), 2.81 (dd, 1H), 2.37 (t, 2H), 2.30 (s, 3H), 2.19 (s, 3H). LRMS ESI [M+H]; 572.9

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel
  8. washeluting with CH2Cl2/MeOH(NH3 2M) 4%

Sources & evidence

ORD record
ord-292b499de3934923a3e6ca71e8ce0280
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

Loading…