Triethylamine → 5-difluoromethyl-2-methyl-4-{2-methyl-5-(3-methyl-methoxy-1-butynyl)-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 1883627노트

반응식

HRID 1883627 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:19])=[C:6]([CH:18]=1)[CH2:7][N:8]1[C:12]([CH:13]([F:15])[F:14])=[N:11][N:10]([CH3:16])[C:9]1=[O:17].C[C:21]([O:25][CH3:26])(C)[C:22]#[CH:23].[C:27]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:28]=1.C(N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I.COC(C)(C)C.C(#N)C>[F:14][CH:13]([F:15])[C:12]1[N:8]([CH2:7][C:6]2[CH:18]=[C:2]([C:27]#[C:28][CH:22]([CH3:23])[CH2:21][O:25][CH3:26])[CH:3]=[CH:4][C:5]=2[CH3:19])[C:9](=[O:17])[N:10]([CH3:16])[N:11]=1

참가 물질

9

반응물 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 49132563-Methoxy-3-methylbut-1-yneHCID 129940064-(5-bromo-2-methylbenzyl)-5-difluoromethyl-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one2회

생성물 1

HCID 1317244995-difluoromethyl-2-methyl-4-{2-methyl-5-(3-methyl-methoxy-1-butynyl)-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one수율 686.9%

시약·촉매·용매 4

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6342Acetonitrile용매HCID 15413tert-Butyl methyl ether용매

실험 절차

498 mg (1.5 mmol) of 4-(5-bromo-2-methylbenzyl)-5-difluoromethyl-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (Compound 40), 378 mg (1.2 mmol) of 3-methyl-3-methoxy-1-butine, 21.1 mg (0.030 mmol) of PdCl2(PPh3)2, 19.0 mg (0.050 mmol) of copper iodide, 39.3 mg (0.15 mmol) of triphenylphosphine, 607 mg of triethylamine and 6.0 ml of acetonitrile were mixed, and the mixture was heated under reflux for 4.5 hours in nitrogen atmosphere. After cooling to room temperature, t-butyl methyl ether was added to the reaction solution, and the mixture was filtrated through celite, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluant: hexane/ethyl acetate=2/1 (v/v)) to obtain 360 mg of 5-difluoromethyl-2-methyl-4-{2-methyl-5-(3-methyl-methoxy-1-butynyl)-benzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (Compound 326).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4.5 hours in nitrogen atmosphere
  3. filtrationthe mixture was filtrated through celite
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f3c8c7914d304070ac449f90d25c0cec
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06762197B2

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