Triethylamine → HCID 49871399, compound

HRID 1951354Notes

Reaction equation

HRID 1951354 reaction equation
CCN(CC)CC.Br[C:9]1[C:10]2[N:11]([CH:21]=[C:22]([CH3:24])[N:23]=2)[CH:12]=[CH:13][C:14]=1[NH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[C:25]1([C:31]#[CH:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>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.CN(C=O)C>[CH2:19]([O:18][C:16]([N:15]1[C:14]2[CH:13]=[CH:12][N:11]3[CH:21]=[C:22]([CH3:24])[N:23]=[C:10]3[C:9]=2[CH:32]=[C:31]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:17])[CH3:20]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 67363252Ethyl N-(8-bromo-2-methylimidazo[1,2-a]pyridin-7-yl)carbamate

Product 1

HCID 49871399HCID 49871399, compoundYield 11%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of Et3N (10 mL), DMF (75 μL), carbamate 19 (215 mg, 0.72 mmol), PdCl2(PPh3)2 (10 mg, 2 mol %) and phenylacetylene (89 mg, 0.87 mmol) stirred 5 min beforehand, CuI (5 mg, 4 mol %) was added and stirring was continued for another 2 min before flushing with Ar. After stirring for 2 days at 60° C., the mixture was concentrated under vacuum. The residue was diluted with water (30 mL) and extracted with CH2Cl2 (3×30 mL). The organic layers were dried (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by chromatography using cyclohexane/EtOAc (4/1, v/v) as eluent to afford compound 20 as an oil (24.8 mg, yield: 11%); 1H NMR (400 MHz, CDCl3) δ 1.06 (t, 3H, J=7.1 Hz), 2.48 (s, 3H), 4.25 (q, 2H, J=7.1 Hz), 7.09 (s, 1H), 7.32 (s, 1H), 7.40 (m, 5H), 7.69 (d, 1H, J=7.3 Hz), 7.87 (d, 1H, J=7.3 Hz); 13C NMR (100 MHz, CDCl3) δ 13.5, 14.2, 63.6, 103.0, 108.1, 109.5, 115.8, 121.5, 127.8, 127.9, 129.0, 132.3, 133.7, 139.7, 140.4, 141.7, 151.3. Anal. Calcd for C19H17N3O2: C, 71.46; H, 5.37; N, 13.16. Found: C, 72.03; H, 5.42; N, 13.25. Further elution afforded starting material 19 (124 mg, 58%).

Workup

  1. stirringstirring
  2. waitwas continued for another 2 min
  3. custombefore flushing with Ar
  4. stirringAfter stirring for 2 days at 60° C.
  5. concentrationthe mixture was concentrated under vacuum
  6. additionThe residue was diluted with water (30 mL)
  7. extractionextracted with CH2Cl2 (3×30 mL)
  8. dry with materialThe organic layers were dried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated under reduced pressure
  11. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-2a164d1c75ee4c5890f39ccd44b78295
Source dataset
uspto-grants-2013_03
Patent number
US08404707B2

Reaction notes

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