Cesium carbonate → HCID 9835583, compound

HRID 2308181Notes

Reaction equation

HRID 2308181 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([Cl:12])=[CH:7][CH:6]=2.[N:13]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[NH:16][CH2:15][CH2:14]2.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[Cl:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[N:4]=[CH:3][C:2]([N:16]1[CH:17]3[CH2:20][CH2:21][N:13]([CH2:19][CH2:18]3)[CH2:14][CH2:15]1)=[CH:11]2

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 3984071,4-Diazabicyclo(3.2.2)nonaneHCID 634876Binap, (A+-)-HCID 153784653-Bromo-6-chloroquinoline

Product 1

HCID 9835583HCID 9835583, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

0.53 g (2.18 mmol) of 3-bromo-6-chloro_quinoline, 0.25 g (2 mmol) of 1,4-diazabicyclo[3.2.2]_nonane, 0.018 g (0.08 mmol) of palladium diacetate, 0.91 g (2.8 mmol) of cesium carbonate and 0.05 g (0.08 mmol) of 2,2′-bis(diphenylphosphino)-1,1′-bi_naphthyl, in 15 ml of tetrahydrofuran, are introduced consecutively into a 50 ml three-necked round-bottomed flask and the reaction mixture is heated at reflux for 26 h.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 26 h.

Sources & evidence

ORD record
ord-148e65db49e24a419adb2e1f30e029d2
Source dataset
uspto-grants-2004_12
Patent number
US06835730B2

Reaction notes

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