Triethylamine → HCID 67047760, compound

HRID 606946Notes

Reaction equation

HRID 606946 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]#[CH:9])[CH:7]=1.[F:10][C:11]1[CH:21]=[CH:20][C:19](I)=[CH:18][C:12]=1[C:13]([N:15]([CH3:17])[CH3:16])=[O:14].C(N(CC)CC)C>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.[Cu]I.C1(C)C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][C:19]2[CH:20]=[CH:21][C:11]([F:10])=[C:12]([CH:18]=2)[C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[CH:5]=[N:4][CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 235008873-Chloro-5-ethynylpyridineHCID 581814352-Fluoro-5-iodo-N,N-dimethylbenzamide

Product 1

HCID 67047760HCID 67047760, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 1140TolueneSolvent

Procedure

Add bis(triphenylphosphine)palladium (II) dichloride (46 mg, 0.07 mmol), copper (I) iodide (25 mg, 0.13 mmol), and 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (200 mg, 1.45 μmmol) to a solution of 2-fluoro-5-iodo-N,N-dimethylbenzamide, (prepared as described in PREPARATION 45), (0.600 g, 2.1 mmol) in triethylamine (4.3 mL, 31 mmol) and place in an oil bath at 70° C. Add toluene (10 mL) and heat for 2 h. Concentrate and purify by silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes, to give the free base of the title compound as a colorless oil. Dissolve the free base in diethyl ether (50 mL) and add 2 M hydrogen chloride in diethyl ether (2.6 mL, 5.2 mmol). Stir for 10 min, concentrate, triturate with diethyl ether and dry to give the title compound as a light yellow solid (350 mg, >99%).

Workup

  1. concentrationConcentrate
  2. custompurify by silica gel chromatography
  3. washeluting with 50:50 ethyl acetate

Sources & evidence

ORD record
ord-3d0c8ea63fbd43008642c16fbe2be126
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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