Potassium Carbonate → HCID 86696367、化合物

HRID 870667ノート

反応式

HRID 870667 の反応式
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH3:16][O:17][C:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)=[O:19].C(=O)([O-])[O-].[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(#N)C.O>[CH2:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:23]3[CH:24]=[CH:25][C:20]([C:18]([O:17][CH3:16])=[O:19])=[CH:21][CH:22]=3)=[CH:3][N:4]=2)[N:7]=1)[CH2:13][CH2:14][CH3:15]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 866963223-Bromo-6-(butylamino)imidazo[1,2-b]pyridazine

生成物 1

HCID 86696367HCID 86696367、化合物収率 67.3%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 18373917Acetonitrile--water (1/1)溶媒

反応条件

温度
145 °C

実験手順

To a mixture of 3-bromo-N-butylimidazo[1,2-b]pyridazin-6-amine (386 mg, 1.43 mmol), (4-(methoxycarbonyl)phenyl)boronic acid (310 mg, 1.72 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (50 mg, 0.07 mmol) and potassium carbonate (296 mg, 2.15 mmol) was added 3:1 acetonitrile/water (5 mL). The resulting mixture was heated at 145° C. (microwave) for 800 s. The reaction was then filtered and concentrated. The residue was dissolved in methanol, and then filtered again. The filtration was finally purified by column chromatography on silica gel (50% ethyl acetate in hexane) to afford methyl 4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)benzoate (312 mg, 67% yield) as a yellow solid: 1H NMR (CHLOROFORM-d) δ: 8.22-8.34 (m, 2H), 8.09-8.20 (m, 2H), 7.93 (s, 1H), 7.71 (d, J=9.6 Hz, 1H), 6.51 (d, J=9.6 Hz, 1H), 3.97 (s, 3H), 3.41-3.53 (m, 2H), 1.72 (t, J=7.2 Hz, 2H), 1.50 (dd, J=15.0, 7.5 Hz, 2H), 1.02 (t, J=7.5 Hz, 3H); LRMS (ESI) m/e 325.2 [(M+H)+, calcd for C18H21N4O2 325.2].

後処理

  1. filtrationThe reaction was then filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in methanol
  4. filtrationfiltered again
  5. filtrationThe filtration
  6. customwas finally purified by column chromatography on silica gel (50% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-ee6592bf9bec41a3a4792d43a46b5901
出典データセット
uspto-grants-2015_03
特許番号
US08969565B2

反応ノート

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