Benzyl Bromide → HCID 89610023, compound

HRID 2175739Notes

Reaction equation

HRID 2175739 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[BH4-].[Na+]>CN(C=O)C.C(O)C.O>[CH2:13]([N:10]1[CH2:11][CH:12]=[C:7]([CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[CH2:8][CH2:9]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 4311764Sodium borohydrideHCID 14743046HCID 14743046, compound

Product 1

HCID 89610023HCID 89610023, compoundYield 106.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 4-(thiophen-2-ylmethyl)pyridine (H) (3.1 g, 11.52 mmol) in DMF (10 mL) was added benzyl bromide (2.16 g, 12.67 mmol) at 20-35° C. and the reaction mixture was allowed to stir at 100° C. for 3 h. Then the reaction mixture was cooled to 20-35° C., diluted with ethanol (30 mL) and NaBH4 (0.65 g, 17.28 mmol) was added slowly portionwise at 0° C. and then heated at 70-80° C. for 2 h. The reaction mixture was rotary evaporated, resultant residue was diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was rotary evaporated under vacuum to get residue which was purified by column chromatography using a mixture of 20% ethyl acetate/hexane as an eluent to get the desired compound as a light brown oily liquid (3.3 g, 67%); 1H NMR (400 MHz, DMSO-d6) δ 7.33-7.28 (m, 5H), 7.28-7.22 (m, 1H), 6.94 (dd, J=3.4, 5.4 Hz, 1H), 6.84-6.82 (m, 1H), 5.46 (s, 1H), 3.51 (s, 2H), 3.46 (s, 2H), 2.87 (s, 2H), 2.46 (t, J=5.9 Hz, 2H), 1.98 (s, 2H).

Workup

  1. temperatureThen the reaction mixture was cooled to 20-35° C.
  2. additionwas added slowly portionwise at 0° C.
  3. temperatureheated at 70-80° C. for 2 h
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. washThe organic layer was washed with brine (50 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customThe filtrate was rotary evaporated under vacuum
  9. customto get residue which
  10. customwas purified by column chromatography
  11. additiona mixture of 20% ethyl acetate/hexane as an eluent

Sources & evidence

ORD record
ord-5c1bfc428f484c4d962f416302eb1858
Source dataset
uspto-grants-2015_06
Patent number
US09062075B2

Reaction notes

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