Triethylamine → HCID 69061534, compound

HRID 734900Notes

Reaction equation

HRID 734900 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[C:4]([CH3:11])[CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[CH:21][C:22]([C:25]#[CH:26])=[N:23][CH:24]=2)=[CH:15][CH:14]=1.C(N(CC)CC)C>C(#N)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[Cu]I>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:20]=[CH:21][C:22]([C:25]#[C:26][C:2]3[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[C:4]([CH3:11])[CH:3]=3)=[N:23][CH:24]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 578453285-(4-Chloro-phenyl)-2-ethynyl-pyridineHCID 690577934-Iodo-2-methylbenzeneethanol

Product 1

HCID 69061534HCID 69061534, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6342AcetonitrileSolvent

Procedure

Under an argon atmosphere 16 mg (0.02 mmol) of PdCl2(dppf) and 4 mg (0.02 mmol) of CuI were added to a repeatedly degassed solution of 940 mg (1.79 mmol) of 2-(4-iodo-2-methylphenyl)ethanol, 383 mg (1.79 mmol) of 5-(4-chlorophenyl)-2-ethynylpyridine (IP 13), and 0.52 mL (3.77 mmol) of triethylamine in 8 mL of acetonitrile and the mixture was stirred overnight at RT. The precipitate was suction filtered and washed with acetonitrile. Yield: 270 mg (43% of theoretical); C22H18ClNO (M=347.837); calc.: molpeak (M+H)+:348/50 (Cl); found: molpeak (M+H)+:348/50 (Cl); HPLC-MS: 6.15 minutes (method H).

Workup

  1. filtrationfiltered
  2. washwashed with acetonitrile
  3. custom6.15 minutes (method H)

Sources & evidence

ORD record
ord-7bf90355ada644a18ff7f8a0653442a4
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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