HCID 11631213, compound → HCID 11588147, compound

HRID 746607Notes

Reaction equation

HRID 746607 reaction equation
[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][C:5]1[S:9][C:8]2[CH:10]=[C:11]([CH3:14])[CH:12]=[CH:13][C:7]=2[C:6]=1[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)=[O:16].[Li][CH3:25]>C1(C)C=CC=CC=1>[CH3:23][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[S:9][C:8]2[CH:10]=[C:11]([CH3:14])[CH:12]=[CH:13][C:7]=2[C:6]=1[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)([OH:16])[CH3:25]

Participants

4

Reactant 2

HCID 11631213HCID 11631213, compoundHCID 178418348HCID 178418348, compound2×

Product 1

HCID 11588147HCID 11588147, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a cooled (−78° C.) solution of [2-(2-dimethylamino-ethyl)-6-methyl-benzo[b]thiophen-3-yl]-pyridin-2-yl-methanone (0.444 g, 1.50 mmol) in anhydrous toluene (5 mL), MeLi (1 mL, 1.6 mmol, 1.6 M in ether) was added and the mixture was stirred while the temperature was kept <−60° C. After 2 hours, an additional aliquot of MeLi (0.2 mL, 0.32 mmol) was added and stirring was continued for another 2 hours. The reaction was quenched with a mixture of 1.3 mL 6N HCl and 2.6 mL MeOH while keeping the temperature <−45° C. The mixture was allowed to warm to room temperature and the organic phase was separated. The organic phase was extracted with 500 mL of 1N HCl. The combined aqueous phases were neutralized with 50% sodium hydroxide and extracted 3 times with ethyl acetate. The combined organic phases were dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (dichloromethane/MeOH=97/3 up to 85/15) afforded 1-[2-(2-dimethylamino-ethyl)-6-methyl-benzo[b]thiophen-3-yl]-1-pyridin-2-yl-ethanol in quantitative yield.

Workup

  1. additionwas added
  2. customwas kept <−60° C
  3. stirringstirring
  4. waitwas continued for another 2 hours
  5. customThe reaction was quenched with a mixture of 1.3 mL 6N HCl and 2.6 mL MeOH
  6. customthe temperature <−45° C
  7. customthe organic phase was separated
  8. extractionThe organic phase was extracted with 500 mL of 1N HCl
  9. extractionextracted 3 times with ethyl acetate
  10. dry with materialThe combined organic phases were dried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-f8f6e777f5ab452782bc29efeb8f9000
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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