Potassium Carbonate → HCID 67355115, compound

HRID 522851Notes

Reaction equation

HRID 522851 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.[CH:12]1(B(O)O)[CH2:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:12]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[N:7][CH:6]=[CH:5]3)[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3136816-BromoisoquinolineHCID 2760897Cyclopropylboronic acid

Product 1

HCID 67355115HCID 67355115, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a degassed solution of 6-bromoisoquinoline (0.9 g, 0.004 mol) in 1,4-dioxane (15 mL) was added cyclopropylboronic acid (0.560 g, 0.007 mol) followed by the addition of degassed aqueous solution of K2CO3 (3.1 g, 0.02 mol) and PdCl2(dppf) (0.190 g, 0.002 mol). The resulting reaction mixture was stirred at 110° C. for 10 h. After completion, the reaction mixture was filtered over Celite® (diatomaceous earth) and the filtrate was concentrated at reduced pressure to obtain crude 6-cyclopropylisoquinoline. Purification was done by silica gel column chromatography eluting with EtOAc in hexanes (10-30%) to afford pure 6-cyclopropyl-isoquinoline (0.500 g, 68%) as yellow liquid.

Workup

  1. customThe resulting reaction mixture
  2. filtrationAfter completion, the reaction mixture was filtered over Celite® (diatomaceous earth)
  3. concentrationthe filtrate was concentrated at reduced pressure

Sources & evidence

ORD record
ord-bef48130cc4a4945b6081f6fc98e6713
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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