Triethylamine → Tert-butyl (4-chloro-3-(cyclohexylethynyl)pyridin-2-yl)carbamate

HRID 1521956Notes

Reaction equation

HRID 1521956 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:3]=1I.[C:17]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)#[CH:18].C(N(CC)CC)C>O1CCCC1.[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>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:3]=1[C:18]#[C:17][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 70263EthynylcyclohexaneHCID 59852886tert-Butyl (4-chloro-3-iodopyridin-2-yl)carbamate

Product 1

HCID 131733115Tert-butyl (4-chloro-3-(cyclohexylethynyl)pyridin-2-yl)carbamate

Reagents, catalysts & solvents 3

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

Procedure

tert-Butyl 4-chloro-3-iodopyridin-2-ylcarbamate (1.0 g, 2.82 mmol) in 10 mL tetrahydrofuran was treated with copper(I) iodide (0.027 g, 0.141 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.099 g, 0.141 mmol) and the mixture was purged with nitrogen for 5 minutes. Ethynylcyclohexane (0.472 mL, 3.67 mmol) and triethylamine (1.179 mL, 8.46 mmol) were added and the mixture was stirred overnight under nitrogen. The mixture was filtered through diatomaceous earth and the filtrate washed with aqueous citric acid (once), water (twice), and brine (once), dried over magnesium sulfate, filtered, and concentrated. Purification by flash chromatography (20% ethyl acetate/hexane) provided the title compound. MS (DCI) m/e 335/337 (M+H)+.

Workup

  1. customthe mixture was purged with nitrogen for 5 minutes
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. washthe filtrate washed with aqueous citric acid (once), water (twice), and brine (once),
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c6ff736f33a24db7a4ef7cba4d64c824
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

Loading…