Ethyl 3-iodobenzoate → Ethyl 3-({3-[2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-YL]phenyl}ethynyl)benzoate

HRID 735450Notes

Reaction equation

HRID 735450 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:10]([CH2:22][C:23]3[C:28]([F:29])=[CH:27][C:26]([F:30])=[CH:25][C:24]=3[F:31])[N:11]=[C:12]3[C:17]=2[CH:16]=[CH:15][CH:14]=[C:13]3[C:18]([F:21])([F:20])[F:19])[CH:6]=[CH:7][CH:8]=1)#[CH:2].I[C:33]1[CH:34]=[C:35]([CH:41]=[CH:42][CH:43]=1)[C:36]([O:38][CH2:39][CH3:40])=[O:37]>C([O-])(=O)C.C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[F:31][C:24]1[CH:25]=[C:26]([F:30])[CH:27]=[C:28]([F:29])[C:23]=1[CH2:22][N:10]1[C:9]([C:5]2[CH:4]=[C:3]([C:1]#[C:2][C:33]3[CH:34]=[C:35]([CH:41]=[CH:42][CH:43]=3)[C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH:8]=[CH:7][CH:6]=2)=[C:17]2[C:12]([C:13]([C:18]([F:21])([F:19])[F:20])=[CH:14][CH:15]=[CH:16]2)=[N:11]1

Participants

5

Reactant 2

HCID 143542Ethyl 3-iodobenzoateHCID 866030133-(3-Ethynylphenyl)-2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazole

Product 1

HCID 86603014Ethyl 3-({3-[2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-YL]phenyl}ethynyl)benzoateYield 46.8%

Reagents, catalysts & solvents 2

HCID 82707Tetrabutylammonium AcetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(3-ethynylphenyl)-2-(2,4,6-trifluorobenzyl)-7-(trifluoromethyl)-2H-indazole (0.103 g, 0.24 mmol), ethyl 3-iodobenzoate (0.042 mL, 0.25 mmol), tetrabutylammonium acetate (0.108 g, 0.36 mmol) and 8.8 mg of tris-(dibenzylidineacetone)-dipalladium in 2 mL of dry DMF was stirred at ambient temperature for 3 hours. The reaction mixture was partitioned with ethyl acetate and H2O. The organic phase was concentrated in vacuo and purified by flash chromatography (silica 60, CH2Cl2-hexane, 1:1) to give the title compound (0.065 g).

Workup

  1. customThe reaction mixture was partitioned with ethyl acetate and H2O
  2. concentrationThe organic phase was concentrated in vacuo
  3. custompurified by flash chromatography (silica 60, CH2Cl2-hexane, 1:1)

Sources & evidence

ORD record
ord-0c34ea2679e5403b99330f3e14893949
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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