Ethyl Acetate → HCID 71547824, compound

HRID 1497435Notes

Reaction equation

HRID 1497435 reaction equation
[N:1]1([CH:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[CH:16]=3)=[CH:11][N:10]=2)[CH2:7][CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1.B(Br)(Br)Br.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>ClCCl>[N:1]1([CH:6]([C:9]2[N:10]=[CH:11][C:12]([C:15]3[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=3)=[CH:13][CH:14]=2)[CH2:7][CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 71547823HCID 71547823, compound

Product 1

HCID 71547824HCID 71547824, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

To a solution of 2-(1-(1H-imidazol-1-yl)propyl)-5-(3-methoxyphenyl) pyridine (0.05 g, 0.17 mmol; prepared as described in Example 7) in dichloromethane (1 mL) was added BBr3 (0.064 g, 0.25 mmol) under nitrogen at 0° C. The reaction was stirred at this temperature for 1 h, allowed to warm to rt and then maintained at rt for another 1 h. The contents were diluted with dichloromethane (100 mL) and then distilled off to obtain crude product. Ice-cold water (100 mL) and dichloromethane (50 mL) were then added to the crude product, the mixture was shaken, and the DCM layer was discarded since the product was in the aqueous layer. To this aqueous layer was added ethyl acetate (100 mL) and saturated sodium bicarbonate solution (150 mL). The organic phase was washed with brine solution (2×50 mL), the layers were separated, and the organic layer was dried over sodium sulphate and distilled off to get the crude product. The product was recrystallized with dichloromethane and hexane to give 3-(6-(1-(1H-imidazol-1-yl)propyl)pyridin-3-yl)phenol (20 mg, 42% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.59 (s, 1H), 8.78 (d, 1H), 7.99 (d, 1H), 7.92 (s, 1H), 7.36 (d, 2H), 7.26 (t, 1H), 7.09 (d, 1H), 7.08 (s, 1H), 6.95 (s, 1H), 6.81 (d, 1H), 5.38 (q, 1H), 2.33 (m, 2H), 0.81 (t, 3H); LC-MS m/z calcd for [M+H]+ 280.14. found 280.0.

Workup

  1. temperaturemaintained at rt for another 1 h
  2. distillationdistilled off
  3. customto obtain crude product
  4. stirringthe mixture was shaken
  5. washThe organic phase was washed with brine solution (2×50 mL)
  6. customthe layers were separated
  7. dry with materialthe organic layer was dried over sodium sulphate
  8. distillationdistilled off
  9. customto get the crude product
  10. customThe product was recrystallized with dichloromethane and hexane

Sources & evidence

ORD record
ord-68461ce887f047e99b0e9026f5ccf3a2
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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