Potassium Carbonate → 8-(Benzyloxy)-2-(7-ethylimidazo[1,2-a]pyridin-3-yl)quinoline

HRID 1095739Notes

Reaction equation

HRID 1095739 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]2[CH:9]=[CH:10][N:11]=[C:5]2[CH:4]=1)[CH3:2].[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[N:28]=[C:27](Cl)[CH:26]=[CH:25]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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>[CH2:12]([O:19][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:29]=1[N:28]=[C:27]([C:9]1[N:6]3[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][C:5]3=[N:11][CH:10]=1)[CH:26]=[CH:25]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 181844637-Ethylimidazo[1,2-a]pyridineHCID 220422348-(Benzyloxy)-2-chloroquinoline

Product 1

HCID 667814498-(Benzyloxy)-2-(7-ethylimidazo[1,2-a]pyridin-3-yl)quinolineYield 112.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 7-ethylimidazo[1,2-a]pyridine (1.18 g, 8.06 mmol), 8-benzyloxy-2-chloroquinoline (2.17 g, 8.06 mmol), potassium carbonate (2.23 g, 16.2 mmol), palladium (II) acetate (90.5 mg, 0.40 mmol), tetrakis(triphenylphosphine)palladium (0) (466 mg, 0.40 mmol), 1,4-dioxane (33 ml) and water (0.33 ml) was heated under a nitrogen atmosphere overnight. The reaction mixture was diluted with water, extracted with CH2Cl2 and EtOAc, and the combined organic extracts were dried over Na2SO4, filtered and concentrated to afford the desired product (3.45 g) as a solid. MS APCI (+) m/z 380.2 (M+1) detected.

Workup

  1. temperaturewas heated under a nitrogen atmosphere overnight
  2. extractionextracted with CH2Cl2 and EtOAc
  3. dry with materialthe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c8670632d03d4a3e83be8ca1536c8b24
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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