Acetonitrile → HCID 24956290, compound

HRID 253457Notes

Reaction equation

HRID 253457 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[C:17]([O:18][CH3:19])=[CH:16][C:15]([CH:20]([C:22]2[C:30]3[C:25](=[N:26][CH:27]=[C:28]([Cl:31])[CH:29]=3)[NH:24][CH:23]=2)O)=[C:14]([Cl:32])[CH:13]=1.C(#N)C.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[Cl:32][C:14]1[C:15]([CH2:20][C:22]2[C:30]3[C:25](=[N:26][CH:27]=[C:28]([Cl:31])[CH:29]=3)[NH:24][CH:23]=2)=[CH:16][C:17]([O:18][CH3:19])=[C:12]([CH:13]=1)[O:11][CH2:10][C:2]1[NH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59803826[4-(1H-benzoimidazol-2-ylmethoxy)-2-chloro-5-methoxy-phenyl]-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

Product 1

HCID 24956290HCID 24956290, compound

Conditions

Temperature
70 °C

Procedure

[4-(1H-Benzoimidazol-2-ylmethoxy)-2-chloro-5-methoxy-phenyl]-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (138, 1.25 g, 0.00266 mol) was dissolved in acetonitrile (100 mL, 2 mol) and trifluoroacetic acid (5.65 mL, 0.0734 mol) and triethylsilane (11.3 mL, 0.0708 mol) were added. The reaction was heated at 70° C. for 2.5 hours. The reaction was concentrated and ethyl acetate and 1M aqueous potassium carbonate were added. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was adsorbed onto silica and purified with silica gel column chromatography, eluting with 0-8% methanol:dichloromethane to provide the desired compound as a solid, which was washed with a minimum of ethyl acetate and hexanes and filtered. The collected solid was dried to provide P-2104 (232 mg, 19%). MS (ESI) [M+H+]+=453.1, 455.1.

Workup

  1. concentrationThe reaction was concentrated
  2. additionethyl acetate and 1M aqueous potassium carbonate were added
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. custompurified with silica gel column chromatography
  7. washeluting with 0-8% methanol

Sources & evidence

ORD record
ord-1d04b9e1951040bdadac02af1cd29d34
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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