Ammonia → HCID 58387863, compound

HRID 2079987Notes

Reaction equation

HRID 2079987 reaction equation
C(N(CC)[CH:5]([CH3:7])[CH3:6])(C)C.Br[C:11]1[CH:30]=[CH:29][C:14]([CH2:15][NH:16][C:17]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[N:25]=[CH:24][CH:23]=[CH:22]3)=[O:18])=[CH:13][CH:12]=1.CN1[CH2:36][CH2:35][CH2:34][C:33]1=O.N.O1CCC[CH2:40]1>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.O>[C:7]1([C:5]#[C:6][C:11]2[CH:30]=[CH:29][C:14]([CH2:15][NH:16][C:17]([C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[N:25]=[CH:24][CH:23]=[CH:22]4)=[O:18])=[CH:13][CH:12]=2)[CH:40]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

10

Reactant 5

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 58387988HCID 58387988, compound

Product 1

HCID 58387863HCID 58387863, compoundYield 24%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

N,N-diisopropylethylamine (0.31 mL, 1.8 mmol) was added to a mixture of the resulting quinoline-6-carboxylic acid 4-bromobenzylamide (200 mg, 0.59 mmol) ethynylbenzene(0.077 mL, 0.70 mmol), copper(I)iodide (catalytic amount), tetrakis(triphenylphosphine)palladium(0) (68 mg, 0.059 mmol) and N-methylpyrrolidinone (4 mL), and the solution was stirred at 100° C. for 30 minutes, and at 120° C. for 50 minutes. After cooling, water, ethyl acetate, tetrahydrofuran and 29% aqueous ammonia solution were added to the reaction mixture for extraction, the organic layer was washed with brine, then, the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4), then, the resulting crudely purified product was washed with diethyl ether to obtain the title compound (50 mg, 0.14 mmol, 24%) as a white solid.

Workup

  1. waitat 120° C. for 50 minutes
  2. temperatureAfter cooling
  3. washthe organic layer was washed with brine
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:4)
  6. washthe resulting crudely purified product was washed with diethyl ether

Sources & evidence

ORD record
ord-c6836d5152cf452f8faa272fa080e06b
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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