Acetic Acid → methyl 5-bromo-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoate

HRID 2208912Notes

Reaction equation

HRID 2208912 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH:20](=O)[CH3:21].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Br:1][C:2]1[CH:3]=[C:4]([N:13]([CH2:20][CH3:21])[CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 70872676methyl 5-bromo-2-methyl-3-((tetrahydro-2H-pyran-4-yl)amino)benzoate

Product 1

HCID 70872485methyl 5-bromo-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzoateYield 93%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of methyl 5-bromo-2-methyl-3-((tetrahydro-2H-pyran-4-yl)amino)benzoate (14 g, 43 mmol) and acetaldehyde (3.75 g, 85 mmol) in dichloroethane (150 mL), was added acetic acid (15.4 g, 256 mmol) and the reaction stirred at room temperature for 20 minutes. Then sodium triacetoxyborohydride (27.0 g, 128 mmol) was added at 0° C. and the reaction stirred at room temperature for 2 h. The solvent was removed under reduced pressure and water added to the residue. Extraction was carried out using DCM and the combined organic layers were dried over sodium sulphate and concentrated under reduced pressure to give crude material was purified by column chromatography to afford the title compound (14 g, 93%).

Workup

  1. stirringthe reaction stirred at room temperature for 2 h
  2. customThe solvent was removed under reduced pressure and water
  3. additionadded to the residue
  4. extractionExtraction
  5. dry with materialthe combined organic layers were dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customto give crude material
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-a937a4d6073c42d2a1fac9cd53777aec
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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