Acetamide → HCID 67510177, 화합물

HRID 623554

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HRID 623554 반응식
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:13]([NH2:16])(=[O:15])[CH3:14].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.O1CCOCC1>[C:13]([NH:16][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:15])[CH3:14]

참가 물질

7

반응물 3

HCID 178AcetamideHCID 62657Potassium Phosphate, TribasicHCID 2759833Methyl 2-Chloro-6-methylisonicotinate

생성물 1

HCID 67510177HCID 67510177, 화합물수율 89%

시약·촉매·용매 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
150 °C

실험 절차

A mixture of methyl 2-chloro-6-methylisonicotinate (2.00 g, 10.8 mmol), acetamide (1.27 g, 21.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.20 g, 0.22 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.37 g, 0.65 mmol), tripotassium phosphate (2.74 g, 12.9 mmol) and 1,4-dioxane (26 mL) is heated by microwave irradiation at 150° C. for 1 hr. After cooling to room temperature, the mixture is filtered through a pad of celite. The filtrate is concentrated under reduced pressure and the residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (4:11:3) to give 1.99 g (89% yield) of the title compound as a yellow solid.

후처리

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture is filtered through a pad of celite
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customthe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (4:11:3)

출처 및 근거

ORD 기록
ord-59773bcf0634409fb3d5a05fc39d70fe
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302991B2

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