Cesium carbonate → Isoquinolin-3-yl-(4-pyrrolidin-1-ylmethyl-pyridin-2-yl)-amine

HRID 1257118

반응식

HRID 1257118 반응식
Cl[C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=1.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[C:16]([NH2:24])[N:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[C:16]([NH:24][C:2]2[CH:7]=[C:6]([CH2:8][N:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)[CH:5]=[CH:4][N:3]=2)[N:15]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 311869Isoquinolin-3-AmineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 581138712-Chloro-4-(pyrrolidin-1-ylmethyl)pyridine

생성물 1

HCID 44612346Isoquinolin-3-yl-(4-pyrrolidin-1-ylmethyl-pyridin-2-yl)-amine

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

2-Chloro-4-pyrrolidin-1-ylmethyl-pyridine (1 eq), isoquinoline-3-ylamine (1 eq), 2.0 eq. of caesium carbonate, 10% (mol) Xantphos and 10% (mol) of Pd2(dba)3 were mixed in toluene (3 ml). The reaction mixture was degassed for three times and then warmed to 100° C. overnight. The reaction mixture was cooled, concentrated and purified by column chromatography eluting 0-10% sat. NH3/MeOH and DCM to afford the title compound.

후처리

  1. customThe reaction mixture was degassed for three times
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated
  4. custompurified by column chromatography
  5. washeluting 0-10% sat. NH3/MeOH and DCM

출처 및 근거

ORD 기록
ord-2ef670a2f98b4f4fa6a72814d3128f0a
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461339B2

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