Triethylamine → HCID 67048219, compound

HRID 606846Notes

Reaction equation

HRID 606846 reaction equation
C(N(CC)CC)C.I[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]#[CH:23])[CH:17]=1>C(OCC)(=O)C.[Cu]I.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[ClH:15].[Cl:15][C:16]1[CH:17]=[C:18]([C:22]#[C:23][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 707143-IodopyridineHCID 1230861-Chloro-3-ethynylbenzene

Product 1

HCID 67048219HCID 67048219, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Add triethylamine (0.55 mL, 3.92 mmol), copper (I) iodide (19 mg, 0.098 mmol) and bis(triphenylphosphine)palladium (II) dichloride (35 mg, 0.049 mmol) to a solution of 3-iodopyridine (200 mg, 0.97 mmol) and 1-chloro-3-ethynylbenzene, (prepared essentially as described in PREPARATION 12), (133.7 mg, 0.98 mmol) in ethyl acetate (1 mL). Stir under nitrogen at room temperature for 18 h, filter through diatomaceous earth, wash with ethyl acetate and dichloromethane, and concentrate. Purify the residue by silica gel chromatography, eluting with 100:0 to 0:100 hexanes:dichloromethane. Treat with a 2 M solution of hydrogen chloride in diethyl ether to give the title compound (202 mg, 83%).

Workup

  1. custom(prepared essentially
  2. filtrationfilter through diatomaceous earth
  3. washwash with ethyl acetate and dichloromethane
  4. concentrationconcentrate
  5. customPurify the residue by silica gel chromatography
  6. washeluting with 100:0 to 0:100 hexanes
  7. additionTreat with a 2 M solution of hydrogen chloride in diethyl ether

Sources & evidence

ORD record
ord-2e3ac4e6cb794dc2ad6813713920d5ff
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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