Potassium tert-butoxide → HCID 59699905, compound

HRID 729822Notes

Reaction equation

HRID 729822 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[CH:9][N:8]([CH2:19][O:20][CH2:21][CH2:22][O:23][CH3:24])[C:5]2=[N:6][CH:7]=1.[Cl-].C(C1C=CC=C(C(C)C)[C:30]=1[C:38]1NC=[C:40]([C:43]2C(C(C)C)=CC=CC=2C(C)C)[NH+:39]=1)(C)C.CC(C)([O-:58])C.[K+]>C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl>[CH3:24][O:23][CH2:22][CH2:21][O:20][CH2:19][N:8]1[C:5]2=[N:6][CH:7]=[C:2]([N:39]3[CH2:40][CH2:43][O:58][CH2:30][CH2:38]3)[CH:3]=[C:4]2[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])=[CH:9]1

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 59699736HCID 59699736, compoundHCID 178439026HCID 178439026, compound

Product 1

HCID 59699905HCID 59699905, compoundYield 656.9%

Reagents, catalysts & solvents 1

HCID 498840Bis(benzonitrile)palladium chlorideCatalyst

Conditions

Temperature
120 °C

Procedure

180 mg (0.5 mmol) of 5-bromo-1-(2-methoxy-ethoxymethyl)-3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine, 10 mg of bis(benzonitrile)palladium(II)-chloride, 11 mg of 2,5-bis-(2,6-di-iso-propylphenyl)imidazolium chloride, and 65 mg of potassium-tert-butoxide were placed in a Smith® vial. The vial was flushed with nitrogen and 3 ml of anhydrous 1,4-dioxane and 70 μl of morpholine were added. The resulting mixture was heated to 120° C. for 14 h. The mixture was cooled to room temperature, adsorbed onto silica gel, and purified by flash chromatorgraphy on silica gel using a gradient of ethyl acetate in hexanes to afford 65 mg (0.17 mmol, 33% yield) of 1-(2-methoxy-ethoxymethyl)-3-(2-methoxy-phenyl)-5-morpholin-4-yl-1H-pyrrolo[2,3-b]pyridine as a colorless oil. 1H-NMR (CDCl3): δ 8.17 (d, J=2.8 Hz, 1H), 7.63 (s, 1H), 7.59 (d, J=2.5 Hz, 1H), 7.54 (dd, J=1.6 Hz, 7.4 Hz, 1H), 7.31 (ddd, J=1.6 Hz, 7.4 Hz, 9 Hz, 1H), 7.07 (ddd, J=1.1 Hz, 7.4 Hz, 7.4 Hz, 1H), 7.03 (d(m), J=8.3 Hz, 1H), 5.71 (s, 2H), 3.87 (s, 3H), 3.68 (m, 2H), 3.49 (m, 2H), 3.35 (s, 3H); MS: m/z 398 [MH+].

Workup

  1. customThe vial was flushed with nitrogen and 3 ml of anhydrous 1,4-dioxane and 70 μl of morpholine
  2. additionwere added
  3. temperatureThe mixture was cooled to room temperature
  4. custompurified by flash chromatorgraphy on silica gel using a gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0b59a8dbdd2f470ead008688efa02e40
Source dataset
uspto-grants-2009_09
Patent number
US07582637B2

Reaction notes

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