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

HRID 1975950ノート

反応式

HRID 1975950 の反応式
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]

参加物

7

反応物 3

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

生成物 1

HCID 22000076n-Methyl-3-o-tolyl-isonicotinamide収率 88.6%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6267332633244c5ea81941f841df1cd3
出典データセット
uspto-grants-2001_05
特許番号
US06225316B1

反応ノート

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