Triethylsilane → 3-(4-Fluoro-phenyl)-2-isopropyl-2,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene

HRID 606626Notes

Reaction equation

HRID 606626 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][C:13]1[C:17]([CH2:18][CH:19]2OCCO2)=[C:16]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[N:15]([CH:31]([CH3:33])[CH3:32])[N:14]=1)C1C=CC=CC=1.[SiH](CC)(CC)CC>C(O)(C(F)(F)F)=O>[F:30][C:27]1[CH:28]=[CH:29][C:24]([C:16]2[N:15]([CH:31]([CH3:33])[CH3:32])[N:14]=[C:13]3[C:17]=2[CH2:18][CH2:19][NH:10][CH2:11][CH2:12]3)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 54754013{2-[4-[1,3]Dioxolan-2-ylmethyl-5-(4-fluoro-phenyl)-1-isopropyl-1H-pyrazol-3-yl]-ethyl}-carbamic acid benzyl ester

Product 1

HCID 113916543-(4-Fluoro-phenyl)-2-isopropyl-2,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of {2-[4-[1,3]dioxolan-2-ylmethyl-5-(4-fluoro-phenyl)-1-isopropyl-1H-pyrazol-3-yl]-ethyl}-carbamic acid benzyl ester (1.0 g, 2.1 mmol) in TFA (10 mL) was treated with Et3SiH (2.5 mL, 21 mmol). After 16 h at 50° C., the solution was concentrated and the residue was purified by FCC to afford the title compound.

Workup

  1. concentrationthe solution was concentrated
  2. customthe residue was purified by FCC

Sources & evidence

ORD record
ord-2004a4cd5c264d75b057c1375fb47b79
Source dataset
uspto-grants-2011_03
Patent number
US07915404B2

Reaction notes

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