Cesium carbonate → HCID 86682737, 화합물

HRID 1755386노트

반응식

HRID 1755386 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 86682737HCID 86682737, 화합물수율 43.7%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-cdc012ac554543f7af7cc5bd9077e1a7
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169259B2

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