1,10-Phenanthroline → HCID 131733933, compound

HRID 710277Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C@H:20]2[O:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]2)[CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[N:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>COCCOC.[Cu]I>[CH2:17]([O:16][C:13]1[N:12]=[CH:11][C:10]([C:9]2[O:19][C:2]3[CH:3]=[C:4]([C@H:20]4[O:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]4)[CH:5]=[CH:6][C:7]=3[N:8]=2)=[CH:15][CH:14]=1)[CH3:18]

Participants

Conditions

Temperature: 125 °C

Procedure

(R)-tert-Butyl 2-(3-bromo-4-(6-ethoxynicotinamido)phenyl)morpholine-4-carboxylate (100 mg, 0.2 mmol), cesium carbonate (130 mg, 0.4 mmol), 1,10-phenanthroline (3.6 mg, 0.02 mmol), copper(I) iodide (1.9 mg, 0.01 mmol) were mixed together in 1,2-dimethoxyethane (2 ml). The suspension was degassed with Argon and was heated overnight under Argon at 125° C. The mixture was cooled and poured into ethylacetate and filtered. The filtrate was absorbed on silica gel and separated by chromatography (gradient 10% to 50% EtOAc in heptane) to afford an off-white solid (34 mg, 40%). MS (ISP): 426.6 ([M+H]+).

Workup

customThe suspension was degassed with Argon
temperatureThe mixture was cooled
additionpoured into ethylacetate
filtrationfiltered
customThe filtrate was absorbed on silica gel
customseparated by chromatography (gradient 10% to 50% EtOAc in heptane)

Sources & evidence

ORD record: ord-2184310d88c64bb0b39969feb2d44919
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181230B2

Reaction notes

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