Trimethylsilyl iodide → (S)-[3-(4-Fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-6-yl]-methanol

HRID 8278

Reaction equation

HRID 8278 reaction equation
C([O:8][CH2:9][C@H:10]1[N:14]2[N:15]=[C:16]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=3)[C:17]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[C:13]2[CH2:12][CH2:11]1)C1C=CC=CC=1.C[Si](I)(C)C>C(Cl)(Cl)Cl.CO>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]2[C:16]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=3)=[N:15][N:14]3[C@H:10]([CH2:9][OH:8])[CH2:11][CH2:12][C:13]=23)=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 66679152(S)-6-benzyloxymethyl-3-(4-fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

Product 1

HCID 9923236(S)-[3-(4-Fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-6-yl]-methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of (S)-6-benzyloxymethyl-3-(4-fluoro-phenyl)-2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (0.3 g, 0.73 mmol) in chloroform (1.0 mL) is added trimethylsilyl iodide (0.173 mL, 1.21 mmol). The mixture is stirred 2 h, diluted with methanol (10 mL), stirred 10 min, and concentrated in vacuo. The residue is taken up in ethyl acetate (50 mL), washed with aqueous sodium thiosulfate (2×50 mL), saturated sodium bicarbonate solution, and brine. The resulting solution is dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue is chromatographed on SiO2 (3% methanol/ethyl acetate) to yield the title compound, 149 mg (64%), as a pale yellow solid.

Workup

  1. stirringstirred 10 min
  2. concentrationconcentrated in vacuo
  3. washwashed with aqueous sodium thiosulfate (2×50 mL), saturated sodium bicarbonate solution, and brine
  4. dry with materialThe resulting solution is dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on SiO2 (3% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-d2b49fdbf8f8460680519fe9c34d4e15
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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