Water → HCID 59774846, compound

HRID 2387276Notes

Reaction equation

HRID 2387276 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=2)[NH:13][CH:12]=1)O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.O>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=2)[NH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 59774812HCID 59774812, compound

Product 1

HCID 59774846HCID 59774846, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To (2,4-dichloro-phenyl)-(5-phenoxy-1H-pyrrolo[9,3-b]pyridin-3-yl)-methanol (33, 30 mg, 0.078 mmol) in acetonitrile (8 mL), triethylsilane (1 mL, 7 mmol) and trifluoroacetic acid (0.5 mL, 7 mmol) were added. The reaction solution was heated to reflux for 4 hours. Then, the reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, water, and brine, dried over anhydrous magnesium sulfate, filtrated and concentrated. The crude material was suspended in acetonitrile (1˜2 mL). The precipitated material was collected with vacuum filtration to provide the compound (P-0037, 13 mg, 45%). MS (ESI) [M+H+]+=369.1 and 371.1.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux for 4 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium bicarbonate, water, and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. filtrationThe precipitated material was collected with vacuum filtration
  9. customto provide the compound (P-0037, 13 mg, 45%)

Sources & evidence

ORD record
ord-44efbb42105c43a7874f95fc508a2154
Source dataset
uspto-grants-2012_09
Patent number
US08268858B2

Reaction notes

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