Toluene → HCID 86731463, compound

HRID 509085Notes

Reaction equation

HRID 509085 reaction equation
Br[C:2]1[C:3]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7]2.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:38]1([CH3:44])C=CC=C[CH:39]=1>O.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]>[CH2:15]([O:14][C:12]([C:8]1[N:9]=[CH:10][C:11]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[C:3]([N:17]1[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])[CH2:21][CH2:22]1)[C:2]=2[CH:44]1[CH2:38][CH2:39]1)=[O:13])[CH3:16]

Participants

6

Reactant 3

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 86731462HCID 86731462, compound

Product 1

HCID 86731463HCID 86731463, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of ethyl 8-bromo-7-(4-(tert-butoxycarbonyl)piperazin-1-yl)isoquinoline-3-carboxylate (464 mg, 1 mmol), C3H4B(OH)2 (860 mg, 10 mmol), Pd(dppf)Cl2 (73 mg, 0.1 mmol) and K3PO4 (636 mg, 3 mmol) in toluene (20 ml) and H2O (2 ml) was stirred at 95° C. overnight. After extraction by EA, the residue was dried with anhydrous Na2SO4, concentrated in vacuo, and purified by silica gel chromatography to afford ethyl-7-(4-(tert-butoxycarbonyl)piperazin-1-yl)-8-cyclopropylisoquinoline-3-carboxylate as a yellow solid (350 mg, yield: 85%).

Workup

  1. extractionAfter extraction by EA
  2. dry with materialthe residue was dried with anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-c02a0dd474164fbf8b899ef193d1fc8b
Source dataset
uspto-grants-2015_08
Patent number
US09096549B2

Reaction notes

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