Methyl iodide → HCID 131735092, compound

HRID 929201Notes

Reaction equation

HRID 929201 reaction equation
IC.[H-].[Na+].[Cl:5][C:6]1[CH:7]=[C:8]2[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:25]([O:35][C@H:36]3[C@H:40]4[O:41][CH2:42][C@@H:43]([OH:44])[C@H:39]4[O:38][CH2:37]3)=[N:24][C:9]2=[N:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1.[CH3:45]COC(C)=O.CCCCCC>CN(C=O)C.CCOC(C)=O>[CH3:45][O:44][C@@H:43]1[CH2:42][O:41][C@@H:40]2[C@H:36]([O:35][C:25]3[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:8]4[C:9]([N:24]=3)=[N:10][C:11]([C:12]3[CH:17]=[CH:16][C:15]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)=[CH:14][CH:13]=3)=[C:6]([Cl:5])[CH:7]=4)[CH2:37][O:38][C@H:39]12

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21226206Ethyl acetate hexaneHCID 89558893(3R,3aR,6R,6aR)-6-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol

Product 1

HCID 131735092HCID 131735092, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Iodomethane (40 μl, 0.640 mmol) and sodium hydride (7.7 mg, 0.193 mmol) were added to a stirred solution of (3R,3aR,6R,6aR)-6-[6-chloro-5-(4-phenylphenyl)-1-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol (35.6 mg, 0.061 mmol) in DMF (0.2 ml). The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was then partitioned between EtOAc (40 ml), water (10 ml), and 2 N HCl (10 ml). The organic layer was washed with water (2×20 ml) and brine (1×10 ml), dried over MgSO4, filtered, and evaporated under reduced pressure to give a pale amber residue. The residue was dissolved in EtOAc and loaded onto a 500 micron 20 cm×20 cm silica gel plate, which was developed using 70% EtOAc/hexane. The silica containing the product bands was collected and eluted with EtOAc (80 ml). The solvent was evaporated under reduced pressure to give the desired product as a colorless residue. LC-MS: calculated for C31H36ClN3O5Si 593.21 observed m/e: 594.24 (M+H)+ (Rt 1.40/2 min)

Workup

  1. customThe reaction mixture was then partitioned between EtOAc (40 ml), water (10 ml), and 2 N HCl (10 ml)
  2. washThe organic layer was washed with water (2×20 ml) and brine (1×10 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give a pale amber residue
  7. customThe silica containing the product bands was collected
  8. washeluted with EtOAc (80 ml)
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8a86ce290c814cbb8c4585baab16e4ac
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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