3-Chlorobenzaldehyde → [2-(3-Chloro-phenyl)-6-trifluoromethyl-imidazo[1,2-a]pyridin-3-yl]-ethyl-amine

HRID 1054333

반응식

HRID 1054333 반응식
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[N+:33]([CH2:35][CH3:36])#[C-:34]>CO.O>[Cl:12][C:13]1[CH:14]=[C:15]([C:16]2[N:9]=[C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:10])[F:11])=[CH:8][N:7]3[C:34]=2[NH:33][CH2:35][CH3:36])[CH:18]=[CH:19][CH:20]=1

참가 물질

7

반응물 4

HCID 114773-ChlorobenzaldehydeHCID 12226Ethane, isocyano-HCID 521998p-Toluenesulfonic acid monohydrateHCID 7358622-Amino-5-(trifluoromethyl)pyridine

생성물 1

HCID 74762712[2-(3-Chloro-phenyl)-6-trifluoromethyl-imidazo[1,2-a]pyridin-3-yl]-ethyl-amine수율 53%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

5-(trifluoromethyl)pyridin-2-amine (100 mg, 617 μmol, Eq: 1.00), 3-chlorobenzaldehyde (91.0 mg, 73.7 μl, 648 μmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (35.2 mg, 185 μmol, Eq: 0.3) were dissolved in MeOH (2.00 mL). The resulting colorless solution was stirred at rt. To this solution was added dropwise isocyanoethane (34.0 mg, 45.9 μl, 617 μmol, Eq: 1.00) and the corresponding yellow solution was stirred for 2 h. To the yellow clear solution was added dropwise water until the mixture got turbid and the product precipitated from the MeOH/water mixture. The solid was filtered off, washed with MeOH/water (1:1) and hexane and dried under vacuum, to give a yellow solid (111 mg, 53.0%). MS: 339.0 [M]+; 1H-NMR (D6-DMSO): δ 8.90 (s, 1H), 8.23 (s, 1H), 8.15 (d, 1H), 7.71 (d, 1H), 7.52 (t, 1H), 7.47-7.36 (m, 2H), 5.17 (t, 1H), 3.02 (m, 2H), 1.12 (t, 3H).

후처리

  1. stirringthe corresponding yellow solution was stirred for 2 h
  2. customthe product precipitated from the MeOH/water mixture
  3. filtrationThe solid was filtered off
  4. washwashed with MeOH/water (1:1) and hexane
  5. customdried under vacuum

출처 및 근거

ORD 기록
ord-542e49cceda14ae18d8f097f0d1ccc24
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394304B2

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