Triethylamine → HCID 57657968, compound

HRID 1099696Notes

Reaction equation

HRID 1099696 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([N:10]=[S@:11]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[O:9])[CH:5]=[N:6][CH:7]=1.[C:27]([C:29]1[CH:30]=[C:31]([NH:35][C:36]([C:38]2[N:42]([CH3:43])[N:41]=[C:40]([CH3:44])[CH:39]=2)=[O:37])[CH:32]=[CH:33][CH:34]=1)#[CH:28].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOC(C)=O.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.[Cu]I>[CH3:43][N:42]1[C:38]([C:36]([NH:35][C:31]2[CH:30]=[C:29]([C:27]#[C:28][C:2]3[CH:3]=[C:4]([C:8]([N:10]=[S@:11]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[O:12])=[O:9])[CH:5]=[N:6][CH:7]=3)[CH:34]=[CH:33][CH:32]=2)=[O:37])=[CH:39][C:40]([CH3:44])=[N:41]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 57657815HCID 57657815, compoundHCID 57657904N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

Product 1

HCID 57657968HCID 57657968, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To the flame-dried 100 mL round bottom flask containing (S)-Methyl 5-{N-[(5-bromopyridin-3-yl)carbonyl]-S-phenylsulfonimidoyl}pentanoate (609 mg, 1.39 mmol), N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide (0.50 g), triethylamine (0.77 mL), bis(triphenylphosphine)palladium(II) dichloride (97.3 mg), and triphenylphosphine (9.1 mg) under nitrogen/hydrogen (1:1) atmosphere at room temperature was added copper(I)iodide (52.8 mg). The resulting reaction mixture was heated and stirred at 60° C. for 1 hour. It was then diluted with EtOAc, washed sequentially with saturated aqueous NaHCO3 (2×), brine (1×), and finally dried with anhydrous sodium sulfate. The solution was decanted and concentrated with silica gel. Chromatography (EtOAc-Hex from 1:2 to 3:2) yielded the title compound as white foam in amount of (712 mg, 86%).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. washwashed sequentially with saturated aqueous NaHCO3 (2×), brine (1×)
  4. dry with materialfinally dried with anhydrous sodium sulfate
  5. customThe solution was decanted
  6. concentrationconcentrated with silica gel

Sources & evidence

ORD record
ord-2e821057c98741ac9cd1076e6c05322c
Source dataset
uspto-grants-2012_03
Patent number
US08143410B2

Reaction notes

Loading…