Benzyl Bromide → HCID 68464188, compound

HRID 501189Notes

Reaction equation

HRID 501189 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][N:2]1[C:14]1[N:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][N:15]=1.CC(C)([O-])C.[K+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C=O)C.CCOC(C)=O>[CH2:30]([N:12]1[C:13]2[CH2:1][N:2]([C:14]3[N:15]=[CH:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:19]=3)[CH2:3][CH2:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 23665647Potassium tert-butoxideHCID 58703314HCID 58703314, compound

Product 1

HCID 68464188HCID 68464188, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of Example 8 (200 mg, mmol) in DMF (mL) was added potassium t-butoxide (150 mg) at 0° C. After stirring at 0° C. for 15 min., benzyl bromide (0.1 mL, mmol) was added slowly. After completion of addition, the reaction mixture was allowed to attain room temperature and stirred for a further 3 hours. After completion of reaction, the reaction mixture was diluted with EtOAc. The organic layer was separated and washed with saturated sodium bicarbonate and water. After drying the organic layer using sodium sulfate, it was concentrated to obtain a crude product that was then purified by column chromatography to obtain methyl 2-(9-benzyl-1,3,4,9-tetrahydro-2H-b-carbolin-2-yl)pyrimidine-5-carboxylate (200 mg, 77.0% yield), m/e=398.9 (M+1).

Workup

  1. additionAfter completion of addition
  2. customto attain room temperature
  3. stirringstirred for a further 3 hours
  4. customAfter completion of reaction
  5. customThe organic layer was separated
  6. washwashed with saturated sodium bicarbonate and water
  7. customAfter drying the organic layer
  8. concentrationwas concentrated
  9. customto obtain a crude product that
  10. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-b160a186dde24a8b852a513d1519eb2b
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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