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3-Bromo-6-chloroimidazo(1,2-b)pyridazine → 6-Chloro-3-(3-methoxypyridazin-4-yl)imidazo[1,2-b]pyridazine

HRID 2279068
ノート
印刷プレビュー

反応式

HRID 2279068 の反応式
Br[C:2]1[N:6]2[N:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH3:12][O:13][C:14]1[N:15]=[N:16][CH:17]=[CH:18][C:19]=1[Sn](CCCC)(CCCC)CCCC>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:19]3[CH:18]=[CH:17][N:16]=[N:15][C:14]=3[O:13][CH3:12])=[CH:3][N:4]=2)[N:7]=1
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

6

反応物 2

HCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 674857293-Methoxy-4-(tributylstannyl)pyridazine

生成物 1

HCID 867023276-Chloro-3-(3-methoxypyridazin-4-yl)imidazo[1,2-b]pyridazine収率 64.2%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 178418397
HCID 178418397、化合物
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3-bromo-6-chloroimidazo[1,2-b]pyridazine (Preparation 1b, 182 mg, 0.78 mmol), 3-methoxy-4-(tributylstannyl)pyridazine (Preparation 8b, 313 mg, 0.78 mmol), copper(I) iodide (15 mg, 0.08 mmol) and dry N,N′-dimethylformamide (4 mL) in a Schlenk vial was subjected to three cycles of evacuation backfilling with argon. Tetrakis(triphenylphosphine)palladium(0) (91 mg, 0.08 mmol) was then added and the resulting mixture was subjected to three further cycles of evacuation backfilling with argon before being stirred at 100° C. for 20 hours. The reaction mixture was cooled down, the solvent was removed under reduced pressure and the residue was purified by flash chromatography (1:1 hexanes/ethyl acetate to 100% ethyl acetate) to give the title compound (131 mg, 64%) as a beige solid.

後処理

  1. temperatureThe reaction mixture was cooled down
  2. customthe solvent was removed under reduced pressure
  3. customthe residue was purified by flash chromatography (1:1 hexanes/ethyl acetate to 100% ethyl acetate)

出典と根拠

ORDレコード
ord-6d5d64b71fbf48d6a37a2caf250cbbf9
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09133200B2

反応ノート

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