Triethylamine → 3-(4-Fluorophenyl)-5-(2-Phenylethynyl)-1H-Indazole

HRID 1353704Notes

Reaction equation

HRID 1353704 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](C1CCCCO1)[N:6]=[C:5]2[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1.C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:53]1([C:59]#[CH:60])[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>C(#N)C>[F:23][C:20]1[CH:19]=[CH:18][C:17]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([C:60]#[C:59][C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)[CH:3]=3)[NH:7][N:6]=2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 80271Tri-o-tolylphosphineHCID 224796801h-Indazole,5-bromo-3-(4-fluorophenyl)-1-(tetrahydro-2h-pyran-2-yl)-

Product 1

HCID 224801623-(4-Fluorophenyl)-5-(2-Phenylethynyl)-1H-IndazoleYield 40.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-bromo-3-(4-fluorophenyl)-1-(tetrahydropyran-2-yl)-1H-indazole (0.375 g, 1.0 mmol), triethylamine (1.5 mL), tri-o-tolylphosphine (0.122 g, 0.4 mmol), tri(dibenzylideneacetone)dipalladium(0) (0.092 g, 0.1 mmol) and phenylacetylene (0.204 g, 2.0 mmol) in dried acetonitrile (10 mL) under nitrogen was heated to reflux overnight. It was quenched with water and extracted with ethyl acetate. The extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was then purified by chromatography (SiO2, 10–15% ethyl acetate/hexane) to provide the title compound (0.127 g, 32% yield). 1H NMR (CDCl3) δ 8.16 (t, 1H), 7.93–7.97 (m, 2H), 7.54–7.64 (m, 4H), 7.34–7.37 (m, 3H), 7.21 (t, 2H) 5.77 (dd, 1H), 4.08 (m, 1H), 3.79 (m, 1H), 2.62 (m, 1H), 2.11–2.21 (m, 2H), 1.57–1.83 (m, 3H); ES-MS (m/z) 397 [M+1]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customIt was quenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was then purified by chromatography (SiO2, 10–15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-08c434ad62bc4c9da77b31503ad943ab
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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