Dimethylformamide → HCID 24771241, compound

HRID 1429596Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)=[N:6][CH:7]=1.Br[C:18]1C=CC(Br)=[CH:20][N:19]=1.C([O-])([O-])=O.[K+].[K+].ClC1C=C(O)[CH:35]=[CH:36][C:37]=1Cl.[CH3:40][N:41]([CH:43]=[O:44])[CH3:42]>O>[Cl:16][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[Cl:15])[O:8][C:5]1[N:6]=[CH:7][C:2]([C:43]([N:41]2[CH2:42][CH2:20][N:19]([CH:36]([CH3:35])[CH3:37])[CH2:18][CH2:40]2)=[O:44])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

5-Bromo-2-(3,4-dichloro-phenoxy)-pyridine. To a solution of 2,5-dibromopyridine (2.412 g, 10.18 mmol) in DMF (50 mL) was added K2CO3 (5.22 g, 37.8 mmol) and 3,4-dichlorophenol (2.66 g, 16.3 mmol). The mixture was heated at 90° C. for 18 h then allowed to cool to room temperature (rt). Water was added and the mixture was extracted with DCM. Purification by FCC provided the desired product (3.23 g, 100%). 1H NMR (400 MHz, CDCl3): 8.21 (dd, J=2.5, 0.8 Hz, 1H), 7.81 (dd, J=8.3, 3.0 Hz, 1H), 7.45 (d, J=8.8 Hz, 1H), 7.26 (d, J=1.5 Hz, 1H), 7.00 (dd, J=9.0, 2.5 Hz, 1H), 6.88 (dd, J=8.8, 0.8 Hz, 1H).

Workup

temperatureto cool to room temperature (rt)
extractionthe mixture was extracted with DCM
customPurification by FCC

Sources & evidence

ORD record: ord-3a127e83d06e4226b37ac12eee67ded5
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940731B2

Reaction notes

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