3-Chlorobenzaldehyde → HCID 74763783, 화합물

HRID 1054326

반응식

HRID 1054326 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 74763783HCID 74763783, 화합물수율 18.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d91c3aad364748d1bede9c65528fd0ba
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394304B2

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