Sodium borohydride → HCID 178521391, compound

HRID 1023851Notes

Reaction equation

HRID 1023851 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:22]=[CH:21][CH:20]=[CH:19][C:7]=2[O:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=2)=[O:11])[N:3]=[CH:2]1.[BH4-].[Na+]>CO>[NH:1]1[CH:5]=[C:4]([C:6]2[CH:22]=[CH:21][CH:20]=[CH:19][C:7]=2[O:8][CH2:9][CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=2)[OH:11])[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178521390HCID 178521390, compound

Product 1

HCID 178521391HCID 178521391, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(2-(1H-imidazol-4-yl)phenoxy)-1-(3-bromophenyl)ethanone (0.025 g, 0.0699 mmol) in MeOH (2 mL) at room temperature, was added NaBH4 (0.349 mmol) and the resulting suspension was stirred for 1.5 h. The reaction was quenched by adding 1N HCl followed by basification with saturated Na2CO3 solution. The product was extracted with EtOAc (3×10 mL), organic extract was dried (Na2SO4) and concentrated under reduced pressure to afford yellow solid. The crude was subjected to column chromatography to afford the final product. Yield 84%. 1H NMR: 3.48 (s, 1H), 4.08 (t, 1H, J=9.39 Hz), 4.40 (dd, 1H, J=3.06, 6.69 Hz), 5.18 (dd, 1H, J=3.48, 5.85 Hz), 6.97 (d, 1H, J=7.59 Hz), 7.04 (d, 1H, J=7.59 Hz), 7.19-7.28 (m, 3H), 7.40 (d, 1H, J=8.73 Hz), 7.46 (d, 1H, J=7.80 Hz), 7.55-7.59 (m, 2H), 7.66 (s, 1H).

Workup

  1. customThe reaction was quenched
  2. additionby adding 1N HCl
  3. extractionThe product was extracted with EtOAc (3×10 mL)
  4. extractionorganic extract
  5. dry with materialwas dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customto afford yellow solid

Sources & evidence

ORD record
ord-b7642fb185eb41d9a300ccd1a42524bc
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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