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

HRID 1257118Notes

Reaction equation

HRID 1257118 reaction equation
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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2ef670a2f98b4f4fa6a72814d3128f0a
Source dataset
uspto-grants-2013_06
Patent number
US08461339B2

Reaction notes

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