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

HRID 31412

반응식

HRID 31412 반응식
[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]

참가 물질

6

반응물 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)

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d4e6a59278a04225b468bb83eac89466
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425555B2

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