Tetrahydrofuran → 4-(1-cyclopentyl-7-fluoro-1H-indazol-3-yl)phenyl ethyl hydrogen phosphate

HRID 1295054Notes

Reaction equation

HRID 1295054 reaction equation
[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][C:13]=3[F:15])[C:8]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[P:23](Cl)(Cl)([O:25][CH2:26][CH3:27])=[O:24].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C1C[O:43]CC1>>[P:23]([OH:43])([O:25][CH2:26][CH3:27])([O:22][C:19]1[CH:18]=[CH:17][C:16]([C:8]2[C:9]3[C:14](=[C:13]([F:15])[CH:12]=[CH:11][CH:10]=3)[N:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[N:7]=2)=[CH:21][CH:20]=1)=[O:24]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 15158Ethyl dichlorophosphateHCID 2733832Lithium HexamethyldisilazideHCID 1355248674-(1-cyclopentyl-7-fluoro-1H-indazol-3-yl)phenol

Product 1

HCID 688833044-(1-cyclopentyl-7-fluoro-1H-indazol-3-yl)phenyl ethyl hydrogen phosphate

Procedure

A solution of 4-(1-cyclopentyl-7-fluoro-1H-indazol-3-yl)phenol (0.30 g, 1.0 mmol), ethyl dichlorophosphate (0.13 mL, 1.1 mmol), and lithiumhexamethyldisilazide (0.183 g, 1.1 mmol) in 10 mL of THF was stirred for 1 hour at ambient temperature. The reaction mixture was quenched with H2O and concentrated in vacuo. The residues were purified by reversed phase HPLC (Column: HS Hyperprep C18 8 u ID 22 mm; solvent gradient 40% to 100% acetonitrile (0.1% TFA) in H2O; flowrate 10 mL/min) to give 0.065 g of the title compound as a white solid.

Workup

  1. customThe reaction mixture was quenched with H2O
  2. concentrationconcentrated in vacuo
  3. customThe residues were purified by reversed phase HPLC (Column: HS Hyperprep C18 8 u ID 22 mm; solvent gradient 40% to 100% acetonitrile (0.1% TFA) in H2O; flowrate 10 mL/min)

Sources & evidence

ORD record
ord-34d47accdb9343e99da7873dfaab5f30
Source dataset
uspto-grants-2007_07
Patent number
US07241791B2

Reaction notes

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