Acetic Acid → HCID 58760957, compound

HRID 857470Notes

Reaction equation

HRID 857470 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH:11]=O)=[C:9]([Br:13])[N:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])[N:7]=1)=[O:5])[CH3:2].[CH:21]([NH2:24])([CH3:23])[CH3:22].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH2:11][NH:24][CH:21]([CH3:23])[CH3:22])=[C:9]([Br:13])[N:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])[N:7]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6363IsopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 57360982HCID 57360982, compound

Product 1

HCID 58760957HCID 58760957, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 5-bromo-1-(2-chloro-phenyl)-4-formyl-1H-pyrazole-3-carboxylic acid ethyl ester (2 g), isopropylamine (0.95 ml) and acetic acid (0.4 ml) in 1,2-dichloroethane (16 ml) was added sodium triacetoxyborohydride (1.8 g) and the resulting slurry was stirred for 18 hours. The reaction was diluted into ethyl acetate, washed with saturated aqueous sodium bicarbonate, brine, dried (Na2SO4) and concentrated in vacuo to afford the title compound (I-1c) as a golden oil, 2.5 g.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-284d9f36fd7c488aa527bde9a7e85f7a
Source dataset
uspto-grants-2006_12
Patent number
US07145012B2

Reaction notes

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