Boron tribromide → HCID 71547910, compound

HRID 1497462Notes

Reaction equation

HRID 1497462 reaction equation
[N:1]1([CH:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=3)=[CH:10][N:9]=2)[CH3:7])[CH:5]=[CH:4][N:3]=[CH:2]1.B(Br)(Br)Br>C(Cl)Cl>[N:1]1([CH:6]([C:8]2[N:9]=[CH:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[CH:12][CH:13]=2)[CH3:7])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 71547909HCID 71547909, compound

Product 1

HCID 71547910HCID 71547910, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(1-(1H-imidazol-1-yl)ethyl)-5-(4-methoxyphenyl)pyridine (0.075 g, 0.26 mmol; prepared as described for Example 15) in DCM (3 mL) was added BBr3 (0.1 mL 0.4 mmol) at 0° C. The reaction was stirred at rt for about 1 h. The reaction mixture was quenched with saturated NaHCO3 solution (5 mL), diluted with water (100 mL), and extracted with DCM (2×100 mL). The combined organic extracts were washed with brine solution (10 mL), organic layer was dried over Na2SO4 and concentrated under vacuum to obtain crude product. The crude product was purified by flash chromatography (silica gel, 60-120) using 4% methanol in DCM eluent to afford 4-(6-(1-(1H-imidazol-1-yl)ethyl)pyridin-3-yl)phenol as an off-white solid (35 mg, 49% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.62 (s, 1H), 8.74 (d, 1H), 7.99 (dd, 1H), 7.85 (s, 1H), 7.50 (d, 2H), 7.28 (s, 1H), 7.20 (d, 1H), 6.91 (s, 1H), 6.84 (d, 2H), 5.64-5.59 (m, 1H), 1.80 (d, 3H), LC-MS m/z calcd for [M+H]+ 266.12. found 266.2.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3 solution (5 mL)
  2. additiondiluted with water (100 mL)
  3. extractionextracted with DCM (2×100 mL)
  4. washThe combined organic extracts were washed with brine solution (10 mL), organic layer
  5. dry with materialwas dried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customto obtain crude product
  8. customThe crude product was purified by flash chromatography (silica gel, 60-120)

Sources & evidence

ORD record
ord-dd64f22c6187482687081884871c196d
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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