Cesium carbonate → 1-[5-(2,6-dimethyl-phenyl)-1-(6-isopropoxy-pyridazin-3-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-one

HRID 472048Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:17]([C:18](=[O:24])[CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:16][NH:15][C:12]2=[CH:13][N:14]=1.Cl[C:26]1[N:27]=[N:28][C:29]([O:32][CH:33]([CH3:35])[CH3:34])=[CH:30][CH:31]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:17]([C:18](=[O:24])[CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:16][N:15]([C:26]3[N:27]=[N:28][C:29]([O:32][CH:33]([CH3:35])[CH3:34])=[CH:30][CH:31]=3)[C:12]2=[CH:13][N:14]=1

Participants

Conditions

Temperature: 149 °C

Procedure

To a solution of 1-[5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-one (100 mg, 0.31 mmol) (Step 4, Example 1) in 2 mL of DMF, 3-chloro-6-isopropoxy-pyridazine (161 mg, 0.93 mmol) is added, followed by Cs2CO3 (306 mg, 0.93 mmol). The mixture is heated to 149° C. for 18 h under nitrogen. The mixture is diluted with EtOAc (7 mL) and washed with water (3×5 mL) and brine (5 mL), dried (Na2SO4), and concentrated under reduced pressure. Chromatography of the residue on silica gel (hexane-EtOAc, 1:1) gives 1-[5-(2,6-dimethyl-phenyl)-1-(6-isopropoxy-pyridazin-3-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-one as colorless oil.

Workup

washwashed with water (3×5 mL) and brine (5 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-b86c6fcf577142feb7331ad7d5e1a653
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633193B2

Reaction notes

Loading…