2,5-Dichlorophenol → HCID 59294546, compound

HRID 1877376Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[OH:28].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O.[Cu]I>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[O:28][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9]

Participants

Conditions

Temperature: 180 °C

Procedure

To a solution of (3-bromo-pyridin-4-yl)-(3,4-dihydro-2H-quinolin-1-yl)-methanone (41.2 mg, 0.13 mmol, 1.0 equiv) and 2,5-dichloro-phenol (21.2 mg, 0.13 mmol, 1.0 equiv; [CAS RN 583-78-8]) in DMAc (1 mL) was added potassium carbonate (35.9 mg, 0.26 mmol, 2.0 equiv; [CAS RN 584-08-7]) and copper(I) iodide (5.0 mg, 0.026 mmol, 0.2 equiv; [CAS RN 7681-65-4]). The reaction mixture was heated by microwave irradiation to 180° C. for 8 h. Purification by preparative HPLC on reversed phase (Xterra® PrepMSC 18, 5 μm, 19×50 mm column equipped with a Gilson Liquid Handler 215 autosampler, two Rainin Dynamax® SD-300 pumps, a Sedex ELSD 75 lightscatter and a Dionex UVD 340S UV detector) eluting with a gradient of acetonitrile/water provided 5 mg (10%) of the title compound. MS (ISP): 399.1 [M+H]+.

Workup

customPurification by preparative HPLC on reversed phase (Xterra® PrepMSC 18, 5 μm, 19×50 mm column
customequipped with a Gilson Liquid Handler 215 autosampler, two Rainin Dynamax® SD-300 pumps
washa Sedex ELSD 75 lightscatter and a Dionex UVD 340S UV detector) eluting with a gradient of acetonitrile/water

Sources & evidence

ORD record: ord-c2fd8318dc7c4473a7bc8abdcac4bc15
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309734B2

Reaction notes

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