1,10-Phenanthroline → HCID 71115244, compound

HRID 468806Notes

Reaction equation

HRID 468806 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH:12][C:13]([CH:15]3[CH2:17][CH2:16]3)=[O:14])[N:8]=[CH:9]2)=[CH:4][CH:3]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[C:32](=O)([O-])[O-:33].[Cs+].[Cs+]>[Cu]I.C(O)C>[CH3:32][O:33][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH:12][C:13]([CH:15]3[CH2:17][CH2:16]3)=[O:14])[N:8]=[CH:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 67974626N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide

Product 1

HCID 71115244HCID 71115244, compoundYield 5.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 702EthanolSolvent

Conditions

Temperature
210 °C

Procedure

N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide (150 mg, 0.52 mmol), copper(I) iodide (90 mg, 0.52 mmol), 1,10-phenanthroline (93 mg, 0.52 mmol) and cesium carbonate (219 mg, 0.67 mmol) were added to ethanol (5 mL) in a stainless container. The resulting mixture was stirred at 210° C. for 5 hours under nitrogen. The reaction mixture was concentrated and purified by prep-HPLC and TLC to give the product (7.2 mg, 5.7%). LCMS (ESI): RT (min)=0.79, M+H+=243.0, method=A. 1H NMR (400 MHz, DMSO-d6): δ 10.76 (s, 1H), 8.99 (s, 1H), 8.35 (s, 1H), 7.77 (d, J=8.8 Hz, 1H), 7.42 (s, 1H), 7.32 (d, J=9.2 Hz, 1H), 3.96 (s, 3H), 2.01 (s, 1H), 0.81-0.79 (m, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by prep-HPLC and TLC

Sources & evidence

ORD record
ord-4e855353922c484dbd665c4a3707a4f9
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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