Sodium Carbonate → n-Methyl-3-o-tolyl-isonicotinamide

HRID 1975950노트

반응식

HRID 1975950 반응식
I[C:2]1[CH:11]=[N:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].[C:18]1([CH3:27])[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:7][NH:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][N:10]=[CH:11][C:2]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH3:27]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 22000069N-methyl-3-iodoisonicotinamide

생성물 1

HCID 22000076n-Methyl-3-o-tolyl-isonicotinamide수율 88.6%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

To a suspension of 450 mg (1.7 mmol) 3-iodo-N-methyl-isonicotinamide in 10 ml toluene were added successively 60 mg (0.05 mmol) tetrakis(triphenylphosphine)palladium(0), 2.5 ml 2 M sodium carbonate solution in water and 342 mg (2.5 mmol) o-tolylboronic acid. The mixture was heated under argon at 80° C. for 20 h. The aqueous layer was separated and washed twice with toluene. The combined organic layers were washed with brine, dried (magnesium sulfate) and evaporated. Chromatography of the residue afforded 341 mg (87%) of the title compound as a light yellow solid. M.p. 90-92° C.

후처리

  1. customThe aqueous layer was separated
  2. washwashed twice with toluene
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated

출처 및 근거

ORD 기록
ord-6267332633244c5ea81941f841df1cd3
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06225316B1

반응 노트

불러오는 중…