Ethyl isocyanate → 4-(1-cyclopentyl-7-fluoro-1H-indazol-3-yl)phenyl ethylcarbamate

HRID 1295052Notes

Reaction equation

HRID 1295052 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.[CH2:23]([N:25]=[C:26]=[O:27])[CH3:24]>O1CCOCC1>[CH2:23]([NH:25][C:26](=[O: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)[CH3:24]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 1355248674-(1-cyclopentyl-7-fluoro-1H-indazol-3-yl)phenol

Product 1

HCID 688829574-(1-cyclopentyl-7-fluoro-1H-indazol-3-yl)phenyl ethylcarbamateYield 74.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-(1-cyclopentyl-7-fluoro-1H-indazol-3-yl)phenol (0.30 g, 1.0 mmol) and ethyl isocyanate (0.080 mL, 1.0 mmol) in 10 mL of dioxane was heated at 80° C. for 48 hours. The reaction mixture was concentrated in vacuo. The residue was crystallized from EtOAc/hexane to give 0.275 g of the title compound as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was crystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-df1045168c6d43668ed8792b2321cbe1
Source dataset
uspto-grants-2007_07
Patent number
US07241791B2

Reaction notes

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