Methanol → HCID 67110835, compound

HRID 540786Notes

Reaction equation

HRID 540786 reaction equation
[C:1](Cl)(=[O:3])C.[Br:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:16]=[C:15]([O:17][C:18]3[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=3)[N:14]([CH2:26][CH3:27])[N:13]=2)[CH:9]=[CH:10][CH:11]=1.[CH3:28]O>>[Br:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:16]=[C:15]([O:17][C:18]3[CH:19]=[CH:20][C:21]([CH:22]([O:3][CH3:1])[O:23][CH3:28])=[CH:24][CH:25]=3)[N:14]([CH2:26][CH3:27])[N:13]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 77231148HCID 77231148, compound

Product 1

HCID 67110835HCID 67110835, compoundYield 89%

Conditions

Temperature
50 °C

Procedure

Acetyl chloride (0.023 ml, 0.323 mmol, 0.1 equiv) was added to a stirring solution of 4-{[3-(3-bromophenyl)-1-ethyl-1H-pyrazol-5-yl]oxy}benzaldehyde (1.2 g, 3.23 mmol, 1.0 equiv) in methanol (7 mL). 4A molecular sieves were added and the mixture was stirred at 50° C. for 3 hours. The sieves were filtered and the filtrate was concentrated. The crude product was purified by flash chromatography on silica gel (0-70% ethyl acetate:hexanes) to give 3-(3-bromophenyl)-5-[4-(dimethoxymethyl)phenoxy]-1-ethyl-1H-pyrazole (1.2 g, 2.88 mmol, 89% yield). Calc'd (M+1)+419.0. Found: 419.19 (minor peak), 373.18 (major peak). Major peak is aldehyde seen because of deprotection occurring on LCMS.

Workup

  1. filtrationThe sieves were filtered
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was purified by flash chromatography on silica gel (0-70% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-a5997421eb9146b096a1fe6712f9d24e
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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