Triethylamine → HCID 69220550, compound
Reaction equation
[C:1]([O:6][CH3:7])(=[O:5])/[CH:2]=[CH:3]/[CH3:4].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.Br[C:38]1[CH:39]=[C:40]2[C:44](=[CH:45][CH:46]=1)[NH:43][N:42]=[C:41]2[C:47]1[CH:52]=[C:51]([CH:53]([CH3:55])[CH3:54])[CH:50]=[C:49]([CH:56]([CH3:58])[CH3:57])[C:48]=1[O:59][CH2:60][CH3:61]>CN(C=O)C.[Cl-].[Na+].O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:7][O:6][C:1](=[O:5])[CH:2]=[C:3]([C:38]1[CH:39]=[C:40]2[C:44](=[CH:45][CH:46]=1)[NH:43][N:42]=[C:41]2[C:47]1[CH:52]=[C:51]([CH:53]([CH3:55])[CH3:54])[CH:50]=[C:49]([CH:56]([CH3:58])[CH3:57])[C:48]=1[O:59][CH2:60][CH3:61])[CH3:4]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 120 °C
Procedure
Methyl crotonate (0.017 mL, 0.17 mmol), tris(dibenzylideneacetone)-dipalladium(0) (1.3 mg, 0.001 mmol), tri-o-tolylphosphine (18.2 mg, 0.06 mmol), and triethyl amine (0.042 mL, 0.30 mmol) were added to a solution of 5-bromo-3-(2-ethoxy-3,5-diisopropyl-phenyl)-1H-indazole (60 mg, 0.15 mmol) in DMF (1 mL). The reaction mixture was then heated to 120° C. under an atmosphere of nitrogen for 12 hrs., then cooled, poured into brine and extracted with ethyl acetate (2×5 mL). The organic was dried over MgSO4 and evaporated to give 3-[3-(2-ethoxy-3,5-diisopropyl-phenyl)-1H-indazol-5-yl]-but-2-enoic acid methyl ester as a clear oil which was used without further purification. MS [EI+] 421 (M+H)+ MS [EI−] 419 (M−H)−.
Workup
- temperature, then cooled
- extractionextracted with ethyl acetate (2×5 mL)
- dry with materialThe organic was dried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-0f12cb8bf3ed45ac88d07c192ad2383a
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07348359B2
Reaction notes
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