Acetic Acid → HCID 23157418, compound

HRID 508066Notes

Reaction equation

HRID 508066 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]([CH2:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=2[O:23][CH2:24][CH:25]([CH3:27])[CH3:26])[CH:18]=O)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[C:31]([F:42])[CH:30]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(OCC)(=O)C>[C:1]([C:5]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]([CH2:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=2[O:23][CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:18][NH:28][C:29]2[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[C:31]([F:42])[CH:30]=2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 23157234Ethyl 3-(4-amino-2-fluorophenyl)propanoateHCID 23157268HCID 23157268, compound

Product 1

HCID 23157418HCID 23157418, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]-4-isobutoxybenzaldehyde (0.43 g, 1.16 mmol) and ethyl 3-(4-amino-2-fluorophenyl)propanoate (0.25 g, 1.16 mmol) in 1,2-dichloroethane (8.6 mL) was added acetic acid (0.20 mL, 3.48 mmol), and the mixture was stirred at room temperature for 3 hr. Sodium triacetoxyborohydride (0.74 g, 3.48 mmol) was added, and the mixture was further stirred for 5 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate and saturated brine, dried, and concentrated under reduced pressure to give the title compound (0.62 g, yield 100%) as a colorless oil.

Workup

  1. stirringthe mixture was further stirred for 5 hr
  2. washwashed with saturated aqueous sodium hydrogencarbonate and saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e18a2b8f49bf4f109c48ca343c5285ad
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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