Triethylamine → HCID 57686175, compound

HRID 1038150Notes

Reaction equation

HRID 1038150 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:4]=1)#[CH:2].I[C:35]1[CH:36]=[N:37][CH:38]=[CH:39][C:40]=1[OH:41].C(N(CC)CC)C.C(OCC)(=O)C>CN(C=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[N+:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]([C:15]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[N:4]=[C:3]2[C:1]1[O:41][C:40]2[CH:39]=[CH:38][N:37]=[CH:36][C:35]=2[CH:2]=1)([O-:14])=[O:13]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 576857343-ethynyl-5-nitro-1-trityl-1H-indazoleHCID 178516478HCID 178516478, compound

Product 1

HCID 57686175HCID 57686175, compoundYield 80%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A reaction mixture containing 3-ethynyl-5-nitro-1-trityl-1H-indazole (215 mg, 0.5 mmol), 3-iodo-pyridin-4-ol (132 mg, 0.6 mmol), copper (I) iodide (4.5 mg, 0.025 mmol), PdCl2(PPh3)2 and triethylamine (120 mg, 1.2 mmol) in DMF (3 mL) was heated at 100° C. overnight under argon. After the completion of reaction (shown by TLC), ethyl acetate (50 mL) was added and the reaction mixture was added to water. The organic layer was collected, washed with water, brine and concentrated under vacuum. After purification using silica (7% methanol in dichloromethane), the desired product was obtained (210 mg, 0.4 mmol) in 80% yield.

Workup

  1. additionwas added
  2. customThe organic layer was collected
  3. washwashed with water, brine
  4. concentrationconcentrated under vacuum
  5. customAfter purification

Sources & evidence

ORD record
ord-b8a89b289cf841ab9de8861c160bb54b
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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