Diisopropylethylamine → 2-Chloro-N-(3-iodo-4-methylphenyl)pyridine-4-carboxamide

HRID 31412

反応式

HRID 31412 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[I:44][C:45]1[CH:46]=[C:47]([CH:49]=[CH:50][C:51]=1[CH3:52])[NH2:48]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([NH:48][C:47]1[CH:49]=[CH:50][C:51]([CH3:52])=[C:45]([I:44])[CH:46]=1)=[O:7]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 1188893-Iodo-p-toluidineHCID 2369852-Chloroisonicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 219145572-Chloro-N-(3-iodo-4-methylphenyl)pyridine-4-carboxamide収率 89.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-Chloroisonicotinic acid (3.3 g, 21 mmol), HATU (8.75 g, 23 mmol), diisopropylethyl amine (10.9 ml, 63 mmol) and 3-iodo-4-methylaniline (5.00 g, 21 mmol) in dimethylformamide (50 ml) were heated under nitrogen for 16 hours. The reaction was cooled, solvent removed in vacuo and the residue taken up in dichloromethane (150 ml). The organic solution was washed with water (3×100 ml) and brine (100 ml), dried over magnesium sulfate, filtered and solvent removed in vacuo. The residue was purified by column chromatography (40:60 ethyl acetate:cyclohexane) to give 2-chloro-N-(3-iodo-4-methylphenyl)-isonicotinamide as a white solid (7.00 g, 18.8 mmol).

後処理

  1. temperatureThe reaction was cooled
  2. customsolvent removed in vacuo
  3. washThe organic solution was washed with water (3×100 ml) and brine (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customsolvent removed in vacuo
  7. customThe residue was purified by column chromatography (40:60 ethyl acetate:cyclohexane)

出典と根拠

ORDレコード
ord-d4e6a59278a04225b468bb83eac89466
出典データセット
uspto-grants-2008_09
特許番号
US07425555B2

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