1,10-Phenanthroline → HCID 57411092, compound

HRID 1502325Notes

Reaction equation

HRID 1502325 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(=O)([O-])[O-].[Cs+].[Cs+].[CH:38]1([OH:42])[CH2:41][CH2:40][CH2:39]1>[Cu]I>[CH:38]1([O:42][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[C:7]([NH:12][C:13]([CH:15]4[CH2:17][CH2:16]4)=[O:14])[N:8]=[CH:9]3)=[CH:4][CH:3]=2)[CH2:41][CH2:40][CH2:39]1

Participants

6

Reactant 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 76218CyclobutanolHCID 67974626N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide

Product 1

HCID 57411092HCID 57411092, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
130 °C

Procedure

N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide (150 mg, 0.51 mmol), copper(I) iodide (96 mg, 0.51 mmol), 1,10-phenanthroline (100 mg, 0.51 mmol) and cesium carbonate (216 mg, 0.62 mmol) were combined in stainless container, and cyclobutanol (3.0 mL) was added. The reaction mixture was stirred at 120-140° C. for 12 h under nitrogen. It was concentrated and purified by HPLC and TLC to give the product (17.1 mg, 12.0%). LCMS (ESI): RT (Min)=1.15, M+H+=282.9, method=A. 1H NMR (400 MHz, DMSO-d6). 10.75 (s, 1H), 8.97 (s, 1H), 8.33 (s, 1H), 7.74 (d, J=9.0 Hz, 1H), 7.26 (d, J=6.8 Hz, 2H), 4.77 (t, J=6.8 Hz, 1H), 2.07-1.65 (m, 6H), 1.19 (s, 1H), 0.79-0.76 (m, 4H).

Workup

  1. additionwas added
  2. concentrationIt was concentrated
  3. custompurified by HPLC and TLC

Sources & evidence

ORD record
ord-e0e3dde5ac78459bbd777f621ce3ce4f
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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