3-Chlorobenzaldehyde → HCID 74763783、化合物

HRID 1054326

反応式

HRID 1054326 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Cl:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[N+:30]([CH:32]1[CH2:34][CH2:33]1)#[C-:31]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:31]([NH:30][CH:32]3[CH2:34][CH2:33]3)=[C:13]([C:12]3[CH:15]=[CH:16][CH:17]=[C:10]([Cl:9])[CH:11]=3)[N:8]=2)[CH:7]=1

参加物

6

反応物 4

HCID 114773-ChlorobenzaldehydeHCID 661742-Amino-5-chloropyridineHCID 521998p-Toluenesulfonic acid monohydrateHCID 2758008Isocyanocyclopropane

生成物 1

HCID 74763783HCID 74763783、化合物収率 18.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

5-chloropyridin-2-amine (100 mg, 778 μmol, Eq: 1.00), 3-chlorobenzaldehyde (115 mg, 93.0 μl, 817 μmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (44.4 mg, 233 μmol, Eq: 0.3) were dissolved in MeOH (1.00 mL) and the intensive yellow solution was stirred for 10 min. To this yellow solution was added dropwise isocyanocyclopropane (52.2 mg, 47.4 μL, 778 μmol, Eq: 1.00) and the corresponding yellow solution was stirred for 2 h. The solvent was removed and the dark red oil was purified twice by flash column chromatography (ethyl acetate in hexanes) to give the product as yellow solid (45 mg, 18.2%). LC/MS (acid polar): 318.1 [M+H]+; 1H-NMR (CDCl3): δ 8.50 (s, 1H), 8.21 (s, 1H), 8.14 (d, 1H), 7.58 (d, 1H), 7.49 (t, 1H), 7.38 (d, 1H), 7.28 (d, 1H), 5.44 (s, 1H), 2.70 (m, 1H), 0.46-0.39 (m, 4H).

後処理

  1. stirringthe corresponding yellow solution was stirred for 2 h
  2. customThe solvent was removed
  3. customthe dark red oil was purified twice by flash column chromatography (ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-d91c3aad364748d1bede9c65528fd0ba
出典データセット
uspto-grants-2016_07
特許番号
US09394304B2

関連ノート

読み込み中…