Ethylene Glycol → HCID 71115234, compound

HRID 1502326Notes

Reaction equation

HRID 1502326 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+].[CH2:38]([OH:41])[CH2:39][OH:40]>[Cu]I>[OH:40][CH2:39][CH2:38][O:41][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 4

HCID 174Ethylene GlycolHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 67974626N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide

Product 1

HCID 71115234HCID 71115234, compoundYield 14.3%

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, 0.52 mmol), copper(I) iodide (96 mg, 0.52 mmol), 1,10-phenanthroline (100 mg, 0.52 mmol) and cesium carbonate (219 mg, 0.67 mmol) were combined in ethylene glycol (5 mL). The resulting mixture was stirred at 120-140° C. overnight under nitrogen. The reaction mixture was concentrated and purified by prep-HPLC to give the product (20.1 mg, 14.3%). LCMS (ESI): RT (min)=0.86, M+H+=273.0, method=A. 1H NMR (400 MHz, DMSO-d6) δ 10.75 (s, 1H), 8.97 (s, 1H), 8.36 (s, 1H), 7.76 (d, J=9.2 Hz, 1H), 7.41 (s, 1H), 7.34 (d, J=9.2 Hz, 1H), 4.93-4.90 (m, 1H), 4.09 (t, J=4.8 Hz, 2H), 3.78-3.74 (m, 2H), 2.03-2.00 (m, 1H), 0.81-0.77 (m, 4H).

Workup

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

Sources & evidence

ORD record
ord-7c5be1107a2749cb83ab87b605f36bbd
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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