1,10-Phenanthroline → HCID 68095381, compound

HRID 468799Notes

Reaction equation

HRID 468799 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.N1[C:31]2[C:22](=[CH:23][CH:24]=[C:25]3[C:30]=2N=CC=C3)C=CC=1.C(=O)([O-])[O-:33].[Cs+].[Cs+]>[Cu]I.C1(O)CCCCC1>[CH:22]1([O:33][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)[CH2:31][CH2:30][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 3

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

Product 1

HCID 68095381HCID 68095381, compoundYield 23.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 7966CyclohexanolSolvent

Conditions

Temperature
150 °C

Procedure

Cyclohexanol (10 mL) was added to a mixture of N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide (150 mg, 0.44 mmol), copper(I) iodide (83.9 mg, 0.44 mmol), 1,10-phenanthroline (79.2 mg, 0.44 mmol) and cesium carbonate (188 mg, 0.58 mmol). The resulting mixture was stirred at 140-160° C. for 2 hours under nitrogen. The reaction mixture was concentrated and purified by prep-HPLC to give the product (31.5 mg, 22.9%). LCMS (ESI): RT=1.141, M+H+=310.9, method=A. 1H NMR (400 MHz, DMSO-d6) δ 10.73 (s, 1H), 8.97 (s, 1H), 8.34 (s, 1H), 7.74 (d, J=9.2 Hz, 1H), 7.45 (s, 1H), 7.31 (d, J=8.8 Hz, 1H), 4.40-4.50 (m, 1H), 2.01-1.98 (m, 3H), 1.80-1.70 (m, 2H), 1.60-1.21 (m, 6H), 0.82-0.78 (m, 4H).

Workup

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

Sources & evidence

ORD record
ord-bff96057c76e4a3584f00f95d23c554b
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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