Triethylsilane → 1-{4'-[4-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethyl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

HRID 1183322Notes

Reaction equation

HRID 1183322 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH:27]([C:29]4[N:30]=[N:31][N:32]([CH2:34][C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[CH:33]=4)O)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].C([SiH](CC)CC)C.FC(F)(F)S(O)(=O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH2:27][C:29]4[N:30]=[N:31][N:32]([CH2:34][C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[CH:33]=4)=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 12052Triethylsilane3×HCID 62406Trifluoromethanesulfonic acidHCID 665793881-(4'-{4-[(1-Benzyl-1H-[1,2,3]triazol-4-yl)-hydroxy-methyl]-3-methyl-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 665793651-{4'-[4-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethyl)-3-methyl-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4′-{4-[(1-Benzyl-1H-[1,2,3]triazol-4-yl)-hydroxy-methyl]-3-methyl-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropanecarboxylic acid ethyl ester (0.123 g, 0.230 mmol) and triethylsilane (0.044 mL, 0.276 mmol) were dissolved in CH2Cl2 (0.5 mL) then trifluoromethanesulfonic acid (0.5 mL) was slowly added. After stirring for 1 hour at room temperature, an additional portion of triethylsilane (0.050 mL) was added and the reaction was heated to 50° C. for 3.5 hours. An additional portion of triethylsilane (1 mL) was added and the reaction continued to stir at 50° C. for 1 hour. The reaction mixture was concentrated, dissolved in CH2Cl2, and filtered through a plug of silica gel. The crude material was then purified via preparatory HPLC to afford the title compound.

Workup

  1. temperaturethe reaction was heated to 50° C. for 3.5 hours
  2. stirringto stir at 50° C. for 1 hour
  3. concentrationThe reaction mixture was concentrated
  4. dissolutiondissolved in CH2Cl2
  5. filtrationfiltered through a plug of silica gel
  6. customThe crude material was then purified via preparatory HPLC

Sources & evidence

ORD record
ord-52b936bd207741f382a4a59f4c3a4338
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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