Dimethylformamide → {2-[3-(t-Butoxycarbonylaminomethyl)-4-cyanophenylimino]-2-[5-ethyl-2-fluoro-3-(2-triisopropylsilanyloxyethoxy)phenyl]-1-methylsulfanylethylidene}carbamic Acid Methyl Ester

HRID 1157953Notes

Reaction equation

HRID 1157953 reaction equation
[CH3:1][O:2][C:3](=[O:37])[N:4]=[C:5]([S:35][CH3:36])[C:6](=[N:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[C:20]([CH2:26][NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:19]=1)[C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]([OH:15])[C:8]=1[F:16].CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:50][CH2:51][O:52][Si:53]([CH:60]([CH3:62])[CH3:61])([CH:57]([CH3:59])[CH3:58])[CH:54]([CH3:56])[CH3:55]>O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:37])[N:4]=[C:5]([S:35][CH3:36])[C:6](=[N:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[C:20]([CH2:26][NH:27][C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[CH:19]=1)[C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]([O:15][CH2:50][CH2:51][O:52][Si:53]([CH:57]([CH3:58])[CH3:59])([CH:54]([CH3:56])[CH3:55])[CH:60]([CH3:61])[CH3:62])[C:8]=1[F:16]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 11450272(2-Iodoethoxy)triisopropylsilaneHCID 72311195{2-[3-(t-Butoxycarbonylaminomethyl)-4-cyanophenylimino]-2-(5-ethyl-2-fluoro-3-hydroxyphenyl)-1-methylsulfanylethylidene}carbamic Acid Methyl Ester

Product 1

HCID 72311196{2-[3-(t-Butoxycarbonylaminomethyl)-4-cyanophenylimino]-2-[5-ethyl-2-fluoro-3-(2-triisopropylsilanyloxyethoxy)phenyl]-1-methylsulfanylethylidene}carbamic Acid Methyl Ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of {2-[3-(t-butoxycarbonylaminomethyl)-4-cyanophenylimino]-2-(5-ethyl-2-fluoro-3-hydroxyphenyl)-1-methylsulfanylethylidene}carbamic acid methyl ester (346 mg) and DMF (6 mL) there were added cesium carbonate (235 mg) and (2-iodoethoxy)triisopropylsilane [CAS No. 93550-77-7] (323 mg) in that order, under a nitrogen atmosphere The mixture was stirred for 40 hours at room temperature, and then ethyl acetate (200 mL) and water (50 mL) were added. The mixture was sufficiently shaken, and then the organic layer was separated oft washed twice with water (50 mL) and once with saturated aqueous sodium chloride (50 mL) in that order, and dried over anhydrous magnesium sulfate. The mixture was filtered to obtain a filtrate, and the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture) to obtain the target compound (406 mg) as an off-white oil.

Workup

  1. stirringThe mixture was sufficiently shaken
  2. customthe organic layer was separated oft
  3. washwashed twice with water (50 mL) and once with saturated aqueous sodium chloride (50 mL) in that order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe mixture was filtered
  6. customto obtain a filtrate
  7. distillationthe solvent in the filtrate was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture)

Sources & evidence

ORD record
ord-12cddd5507c34a86964a63603ecd41b4
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

Loading…