Triethylamine → HCID 57961596, compound

HRID 541837Notes

Reaction equation

HRID 541837 reaction equation
I[C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[C:23]([C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=1)[NH2:28])#[CH:24]>O1CCCC1.O.[Cu]I.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>[NH2:28][C:27]1[CH:26]=[C:25]([C:23]#[C:24][C:2]2[CH:7]=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:4][N:3]=2)[CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 104682Benzenamine, 3-ethynyl-HCID 24229174tert-Butyl (2-iodopyridin-4-yl)carbamate

Product 1

HCID 57961596HCID 57961596, compoundYield 89%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl (2-iodopyridin-4-yl)carbamate (2.41 g, 7.5 mmol), copper(I) iodide (50 mg, 0.3 mmol) and bis(triphenylphosphine)palladium(II) chloride (200 mg, 0.3 mmol) were stirred in tetrahydrofuran (22 mL) with triethylamine (1.1 mL, 8.1 mmol) under N2 at rt. 3-Ethynylaniline (0.75 mL, 7.2 mmol) was added and the mixture was stirred at rt for 40 hours. The reaction mixture was diluted with water. After removal of the solvent, the aqueous residue was extracted with EtOAc three times, followed by drying, filtration, and concentration to give the desired product as a brown solid (1.97 g, 89%). LCMS for C18H20N3O2 (M+H)+: m/z=310.1.

Workup

  1. customAfter removal of the solvent
  2. extractionthe aqueous residue was extracted with EtOAc three times
  3. customby drying
  4. filtrationfiltration, and concentration

Sources & evidence

ORD record
ord-e8db9e7fb8414773aa4185cfde478a14
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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