5-Bromo-2-methoxybenzyl alcohol → HCID 59497514, compound

HRID 1747346Notes

Reaction equation

HRID 1747346 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]1=[O:19])[CH2:7][CH2:8][CH3:9])C.[Br:21][C:22]1[CH:23]=[CH:24][C:25]([O:30][CH3:31])=[C:26]([CH2:28]O)[CH:27]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:21][C:22]1[CH:23]=[CH:24][C:25]([O:30][CH3:31])=[C:26]([CH:27]=1)[CH2:28][N:12]1[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:10]([CH:6]([CH2:7][CH2:8][CH3:9])[CH2:5][C:4]([OH:3])=[O:20])[C:11]1=[O:19]

Participants

5

Reactant 3

HCID 6122985-Bromo-2-methoxybenzyl alcoholHCID 5363146Diisopropyl azodicarboxylateHCID 594972633-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester

Product 1

HCID 59497514HCID 59497514, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

3-(2-Oxo-2,3-dihydro-benzoimidazol-1-yl)-hexanoic acid ethyl ester (96.7 mg, 0.35 mmol), prepared as described above, (5-bromo-2-methoxy-phenyl)-methanol (152 mg, 0.7 mmol) and triphenylphosphene (183.6, 0.7 mmol) were combined in a reaction vial and THF (1 mL) was added. The mixture was stirred until complete solution was attained, then cooled to 0° C., and diisopropylazodicarboxylate (0.136 mL, 0.7 mmol) was added dropwise. The reaction mixture was agitated at room temperature overnight, diluted with THF (2 mL) then treated directly with the Amberlyst® resin (3 g, 4 mmol). This reaction mixture was agitated overnight and the resin was then filtered and washed with DMF (2×3 mL) and several portions of methanol. The product was eluted by treating the resin with a 20% solution of formic acid in methanol (5 mL) and washing with methanol (3 mL). The combined eluant and final wash was evaporated to provide the title compound (154 mg, 99%). LCMS (ESMS): m/z 447/9 (M+H+).

Workup

  1. additionwas added
  2. stirringThe reaction mixture was agitated at room temperature overnight
  3. stirringThis reaction mixture was agitated overnight
  4. filtrationthe resin was then filtered
  5. washwashed with DMF (2×3 mL) and several portions of methanol
  6. washThe product was eluted
  7. additionby treating the resin with a 20% solution of formic acid in methanol (5 mL)
  8. washwashing with methanol (3 mL)
  9. washThe combined eluant and final wash
  10. customwas evaporated

Sources & evidence

ORD record
ord-34172552329748f786518986d6ac0a29
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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