Triethylamine → HCID 69058356, compound

HRID 734830Notes

Reaction equation

HRID 734830 reaction equation
C(N(CC)CC)C.I[C:9]1[CH:21]=[CH:20][C:12]2[S:13][C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:15][C:11]=2[CH:10]=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:30]=[CH:31][C:32]([C:35]#[CH:36])=[N:33][CH:34]=2)=[CH:25][CH:24]=1.CCOC(C)=O>C1COCC1.[Cu]I>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[CH:30]=[CH:31][C:32]([C:35]#[C:36][C:9]3[CH:21]=[CH:20][C:12]4[S:13][C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:15][C:11]=4[CH:10]=3)=[N:33][CH:34]=2)=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 19007488Methyl 5-iodo-1-benzothiophene-2-carboxylateHCID 578453285-(4-Chloro-phenyl)-2-ethynyl-pyridine

Product 1

HCID 69058356HCID 69058356, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere 3.7 mL (26.72 mmol) of triethylamine was added to a solution of 3.4 g (10.69 mmol) of methyl 5-iodobenzo[b]thiophen-2-carboxylate and 2.48 g (10.69 mmol) of 5-(4-chlorophenyl)-2-ethynylpyridine in 20 mL of THF and the reaction mixture was evacuated three times and in each case gassed with argon. Then 195 mg (0.267 mmol) of PdCl2(dppf)*DCM complex and 51 mg (0.267 mmol) of CuI were added and the reaction mixture was stirred for 70 hours at RT. EtOAc was added, and the precipitated product was filtered off, washed with a little EtOAc, and dried in the air. Yield: 3.0 g (70% of theoretical); C23H14ClNO2S (M=403.881); calc.: molpeak (M+H)+: 404/406 (Cl); found: molpeak (M+H)+: 404/406 (Cl); HPLC-MS: 7.3 minutes (method B).

Workup

  1. customthe reaction mixture was evacuated three times
  2. filtrationthe precipitated product was filtered off
  3. washwashed with a little EtOAc
  4. customdried in the air
  5. custom7.3 minutes (method B)

Sources & evidence

ORD record
ord-b61885f642e54f378a06c87d5236a8e0
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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