Allyl iodide → HCID 90067174, compound

HRID 929150Notes

Reaction equation

HRID 929150 reaction equation
[CH2:1](I)[CH:2]=[CH2:3].[H-].[Na+].[Cl:7][C:8]1[CH:9]=[C:10]2[N:28]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:27]([O:37][C@H:38]3[C@H:42]4[O:43][CH2:44][C@@H:45]([OH:46])[C@H:41]4[O:40][CH2:39]3)=[N:26][C:11]2=[N:12][C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1.CCOC(C)=O.CCCCCC>CN(C=O)C>[CH2:1]([O:46][C@@H:45]1[CH2:44][O:43][C@@H:42]2[C@H:38]([O:37][C:27]3[N:28]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:10]4[C:11]([N:26]=3)=[N:12][C:13]([C:14]3[CH:15]=[CH:16][C:17]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[CH:18][CH:19]=3)=[C:8]([Cl:7])[CH:9]=4)[CH2:39][O:40][C@H:41]12)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 21226206Ethyl acetate hexane2×HCID 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 90067174HCID 90067174, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Allyl iodide (130 μl, 1.422 mmol) and sodium hydride (16.0 mg, 0.400 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-hexahydro-furo[3,2-b]furan-3-ol (82.8 mg, 0.143 mmol) in DMF (1.4 ml). The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was partitioned between EtOAc (75 ml), water (20 ml), and 2 N HCl (10 ml). The organic layer was washed with water (2×30 ml, brine was added to each wash to break an emulsion) and brine (1×20 ml), dried over MgSO4, filtered, and evaporated under reduced pressure to give an amber residue. Flash chromatography of the residue utilizing a 4 g silica RediSep Rf® column and employing a 0-40% EtOAc/hexane gradient followed by 40% EtOAc/hexane afforded the title compound as a pale yellow solid. LC-MS: calculated for C33H38ClN3O5Si 619.23 observed m/e: 620.32 (M+H)+ (Rt 1.43/2 min).

Workup

  1. customThe reaction mixture was partitioned between EtOAc (75 ml), water (20 ml), and 2 N HCl (10 ml)
  2. washThe organic layer was washed with water (2×30 ml, brine
  3. additionwas added to
  4. washeach wash
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto give an amber residue

Sources & evidence

ORD record
ord-c180730f0ca9435392857bd023991be0
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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