Cesium carbonate → HCID 86682737、化合物

HRID 1755386ノート

反応式

HRID 1755386 の反応式
Br[C:2]1[C:3]2[N:4]([CH:9]=[CH:10][N:11]=2)[N:5]=[C:6]([Cl:8])[CH:7]=1.[C:12]([CH:16]1[CH2:20][CH2:19][N:18]([C:21]2[N:26]=[C:25]([NH2:27])[CH:24]=[CH:23][CH:22]=2)[CH2:17]1)([CH3:15])([CH3:14])[CH3:13].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[C:12]([CH:16]1[CH2:20][CH2:19][N:18]([C:21]2[N:26]=[C:25]([NH:27][C:2]3[C:3]4[N:4]([CH:9]=[CH:10][N:11]=4)[N:5]=[C:6]([Cl:8])[CH:7]=3)[CH:24]=[CH:23][CH:22]=2)[CH2:17]1)([CH3:15])([CH3:13])[CH3:14]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 468352698-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 86682736HCID 86682736、化合物

生成物 1

HCID 86682737HCID 86682737、化合物収率 43.7%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (573 mg, 2.47 mmol), 6-(3-tert-butylpyrrolidin-1-yl)pyridin-2-amine (540 mg, 2.47 mmol), Pd2(dba)3 (142 mg, 0.25 mmol), BINAP (307 mg, 0.50 mmol), Cs2CO3 (2.4 g, 7.41 mmol) and dioxane (20 mL) was heated to reflux with stirring for 15 h under N2. The solvent was removed in vacuo and the resulting mixture was purified by chromatography (silica gel, 200-300 mesh, dichloromethane:MeOH=50:1) to give N-(6-(3-tert-butylpyrrolidin-1-yl)pyridin-2-yl)-6-chloroimidazo[1,2-b]pyridazin-8-amine (400 mg, crude) as a brown oil. LC-MS: [M+H]+, 371.1, tR=2.23 min.

後処理

  1. temperaturewas heated
  2. temperatureto reflux
  3. customThe solvent was removed in vacuo
  4. customthe resulting mixture was purified by chromatography (silica gel, 200-300 mesh, dichloromethane:MeOH=50:1)

出典と根拠

ORDレコード
ord-cdc012ac554543f7af7cc5bd9077e1a7
出典データセット
uspto-grants-2015_10
特許番号
US09169259B2

反応ノート

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