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Sodium Carbonate → N-(6-(3-(4-Methylphenylsulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide

HRID 1162432
ノート
印刷プレビュー

反応式

HRID 1162432 の反応式
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([NH:11][C:12](=[O:14])[CH3:13])[N:10]=2)[N:7]=1.[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28](B3OC(C)(C)C(C)(C)O3)[CH:27]=2)(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[CH3:15][C:16]1[CH:17]=[CH:18][C:19]([S:22]([NH:25][C:26]2[CH:31]=[C:30]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([CH:8]=[C:9]([NH:11][C:12](=[O:14])[CH3:13])[N:10]=4)[N:7]=3)[CH:29]=[CH:28][CH:27]=2)(=[O:24])=[O:23])=[CH:20][CH:21]=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 3

HCID 10340Sodium CarbonateHCID 162177213-(p-Toluenesulfonylamino)phenylboronic acid pinacol esterHCID 59519510N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide

生成物 1

HCID 44124523N-(6-(3-(4-Methylphenylsulfonamido)phenyl)imidazo[1,2-b]pyridazin-2-yl)acetamide

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a 10-mL, round-bottomed flask was added N-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetamide from Step 4 (0.060 g, 0.28 mmol), 4-methyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzenesulfonamide (0.19 g, 0.51 mmol, Aldrich, St. Louis, Mo.), DMF (3.0 mL), and aq. sodium carbonate (0.85 mL, 1.7 mmol, 2 M). The mixture was carefully evacuated and backfilled with N2. Bis(triphenylphosphine)palladium(II) chloride (20 mg, 0.028 mmol, Strem Chemical, Inc., Newburyport, Mass.) was added. Once again, the mixture was carefully evacuated and backfilled with N2. The mixture was stirred at 100° C. for 2 h and then allowed to cool to room temperature. The mixture was poured into water (75 mL) and extracted with EtOAc (3×75 mL). The combined extracts were washed with water (2×50 mL) and brine (50 mL) then dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (1 to 5% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound as an off-white solid. MS (ESI positive ion) m/z: 422 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 10.92 (s, 1H), 10.44 (s, 1H), 8.26 (s, 1H), 8.05 (d, J=9.6 Hz, 1H), 7.77 (t, J=1.8 Hz, 1H), 7.67-7.71 (m, 3H), 7.61 (d, J=9.6 Hz, 1H), 7.40 (t, J=7.9 Hz, 1H), 7.35 (d, J=8.0 Hz, 2H), 7.19 (dd, J=8.0 Hz, 1.4 Hz, 1H), 2.32 (s, 3H), 2.11 (s, 3H).

後処理

  1. customThe mixture was carefully evacuated
  2. customOnce again, the mixture was carefully evacuated
  3. temperatureto cool to room temperature
  4. additionThe mixture was poured into water (75 mL)
  5. extractionextracted with EtOAc (3×75 mL)
  6. washThe combined extracts were washed with water (2×50 mL) and brine (50 mL)
  7. dry with materialthen dried (Na2SO4)
  8. concentrationconcentrated onto silica
  9. customPurification by silica gel chromatography (1 to 5% MeOH (2 M in NH3)/CH2Cl2)

出典と根拠

ORDレコード
ord-4c244a75a61245e09554f016448e7e4c
出典データセット
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07820665B2

反応ノート

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