HCID 178509964、化合物 → 3,5-Dichloro-4-(7-chloropyrazolo[4,3-c]pyridin-2-yl)benzonitrile

HRID 626707ノート

反応式

HRID 626707 の反応式
[N:1]([C:4]1[C:9]([Cl:10])=[CH:8][N:7]=[CH:6][C:5]=1/[CH:11]=[N:12]/[C:13]1[C:20]([Cl:21])=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=1[Cl:22])=[N+]=[N-]>C1(C)C=CC=CC=1>[Cl:22][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([Cl:21])[C:13]=1[N:12]1[CH:11]=[C:5]2[CH:6]=[N:7][CH:8]=[C:9]([Cl:10])[C:4]2=[N:1]1)[C:17]#[N:18]

参加物

3

反応物 1

HCID 178509964HCID 178509964、化合物

生成物 1

HCID 696716223,5-Dichloro-4-(7-chloropyrazolo[4,3-c]pyridin-2-yl)benzonitrile収率 71%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A suspension of 4-{[1-(4-azido-5-chloropyridin-3-yl)meth-(E)-ylidene]amino}-3,5-dichlorobenzonitrile (3.8 g, 10.95 mmol) in toluene (45 mL) was heated to reflux for 18 hours and then cooled to room temperature. The precipitated solid was removed by filtration and washed sequentially with toluene, ethyl acetate and DCM. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-100% ethyl acetate in cyclohexane) and then triturated with diethyl ether to afford the title compound as an off-white solid (2.5 g, 71% yield). 1H NMR (400 MHz, CDCl3): δ 9.30 (s, 1H), 8.46 (s, 1H), 8.42 (s, 1H), 7.86 (s, 2H).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. customThe precipitated solid was removed by filtration
  4. washwashed sequentially with toluene, ethyl acetate and DCM
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography (0-100% ethyl acetate in cyclohexane)
  7. customtriturated with diethyl ether

出典と根拠

ORDレコード
ord-d2f2111e5527486bb52e47ae961f97e2
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

反応ノート

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