Triethylamine → HCID 131735699, compound

HRID 2199630Notes

Reaction equation

HRID 2199630 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[N:16]=[N:15][C:14]([C:17]2[CH:18]=[N:19][CH:20]=[C:21](I)[CH:22]=2)=[N:13]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:24]([C:26]1[CH:27]=[C:28]([NH:32][C:33]([C:35]2[O:36][CH:37]=[CH:38][C:39]=2[CH3:40])=[O:34])[CH:29]=[CH:30][CH:31]=1)#[CH:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.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.[Cu]I>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[N:16]=[N:15][C:14]([C:17]2[CH:22]=[C:21]([C:25]#[C:24][C:26]3[CH:27]=[C:28]([NH:32][C:33]([C:35]4[O:36][CH:37]=[CH:38][C:39]=4[CH3:40])=[O:34])[CH:29]=[CH:30][CH:31]=3)[CH:20]=[N:19][CH:18]=2)=[N:13]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 51337833N-(3-ethynylphenyl)-3-methylfuran-2-carboxamideHCID 131735698HCID 131735698, compound

Product 1

HCID 131735699HCID 131735699, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the nitrogen bubbled solution of 3-(2-(3-((tert-butyldimethylsilyl)oxy)propyl)-2H-tetrazol-5-yl)-5-iodopyridine (89 mg, 0.2 mmol, 1 eq), N-(3-ethynylphenyl)-3-methylfuran-2-carboxamide (67.5 mg, 1.5 eq), triphenylphosphine (1.3 mg, 0.025 eq), and triethylamine (0.09 mL, 3 eq) in anhydrous DMF (2 mL) was added bis(triphenylphosphine)palladium(II) dichloride (14 mg, 0.1 eq), and copper(I) iodide (8 mg, 0.2 eq). After the reaction mixture was stirred at room temperature for 20 minutes, it was diluted with ethyl acetate, washed sequentially with saturated aqueous sodium bicarbonate, aqueous ammonium chloride, brine, and dried with anhydrous sodium sulfate. The upper liquor was decanted, concentrated under reduced pressure, and the resulting brown oily residue was loaded onto silica and columned (EtOAc-Hex 1:20 to 1:4). The fractions containing the desired product were collected, concentrated to a lesser amount, and the white fluffy solid was filtered giving N-(3-((5-(2-(3-((tert-butyldimethylsilyl)oxy)propyl)-2H-tetrazol-5-yl)pyridin-3-yl)ethynyl)phenyl)-3-methylfuran-2-carboxamide in an the amount of 78 mg.

Workup

  1. washwashed sequentially with saturated aqueous sodium bicarbonate, aqueous ammonium chloride, brine
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThe upper liquor was decanted
  4. concentrationconcentrated under reduced pressure
  5. additionThe fractions containing the desired product
  6. customwere collected
  7. concentrationconcentrated to a lesser amount
  8. filtrationthe white fluffy solid was filtered

Sources & evidence

ORD record
ord-db726014b54a47e09f7c786683002ed0
Source dataset
uspto-grants-2016_06
Patent number
US09359336B2

Reaction notes

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