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Sodium Methoxide → 8-(1-Ethyl-propyl)-3-(3-methoxy-thieno[3,2-b]pyridin-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

HRID 226080
ノート
印刷プレビュー

反応式

HRID 226080 の反応式
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[C:11]1[N:15]2[N:16]=[C:17]([CH3:25])[CH:18]=[C:19]([CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[C:14]2=[N:13][C:12]=1[CH3:26].[CH3:27][O-:28].[Na+]>[Cu]I.CO>[CH2:21]([CH:20]([C:19]1[C:14]2[N:15]([C:11]([C:3]3[S:4][C:5]4[C:6](=[N:7][CH:8]=[CH:9][CH:10]=4)[C:2]=3[O:28][CH3:27])=[C:12]([CH3:26])[N:13]=2)[N:16]=[C:17]([CH3:25])[CH:18]=1)[CH2:23][CH3:24])[CH3:22]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 10942334Sodium MethoxideHCID 577526393-(3-Bromo-thieno[3,2-b]pyridin-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

生成物 1

HCID 577525918-(1-Ethyl-propyl)-3-(3-methoxy-thieno[3,2-b]pyridin-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine収率 45%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 887
Methanol
溶媒

反応条件

温度
120 °C

実験手順

50 mg of 3-(3-Bromo-thieno[3,2-b]pyridin-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.12 mmol) and 13 mg of sodium methoxide (0.24 mmol) and 22 mg of copper (I) iodide (0.12 mmol) are placed into 4 ml reaction vial with 3.0 ml of dry MeOH. The reaction vial is capped with a Teflon cap and heated at 120° C. overnight. The reaction mixture is filtered, and water and CH2Cl2 are added. The separated CH2Cl2 is dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (1st column; Hexane:AcOEt:2M NH3 in MeOH=20:4:1, 2nd column; CH2Cl2:Hexane:Acetnitrile=5:4:1) to give the title compound 20 mg (45%). mass spectrum (m/e): 381; 1H-NMR (CDCl3): 8.72 (m, 1H), 8.10 (m, 1H), 7.29 (dd, 1H, J=4.6 Hz, 8.3 Hz), 6.72 (s, 1H), 4.03 (s, 3H), 3.34 (m, 1H), 2.55 (s, 3H), 2.54 (s, 3H), 1.84 (m, 4H), 0.88 (t, 6H, J=7.6 Hz) ppm.

後処理

  1. customThe reaction
  2. customcap
  3. filtrationThe reaction mixture is filtered
  4. additionwater and CH2Cl2 are added
  5. dry with materialThe separated CH2Cl2 is dried over Na2SO4
  6. customevaporated

出典と根拠

ORDレコード
ord-8d33ba9f857e444ba03fcd609030cb20
出典データセット
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07557103B2

反応ノート

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