Cesium carbonate → 4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-7-(tetrahydro-furan-2-ylmethoxy)-quinoline

HRID 8244Notes

Reaction equation

[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][O:7]S(C)(=O)=O.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[C:19]([C:26]2[C:35]3[C:30](=[CH:31][C:32](O)=[CH:33][CH:34]=3)[N:29]=[CH:28][CH:27]=2)=[C:20]2[CH2:25][CH2:24][CH2:23][N:21]2[N:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[C:19]([C:26]2[C:35]3[C:30](=[CH:31][C:32]([O:7][CH2:6][CH:2]4[CH2:3][CH2:4][CH2:5][O:1]4)=[CH:33][CH:34]=3)[N:29]=[CH:28][CH:27]=2)=[C:20]2[CH2:25][CH2:24][CH2:23][N:21]2[N:22]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of methanesulfonic acid tetrahydro-furan-2-ylmethyl ester (0.70 g, 3.66 mmol), 4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ol (400 mg, 1.22 mmol), and cesium carbonate (2.38 g, 7.32 mmol) in N,N-dimethylformamide (2.5 mL) is heated at 60° C. for 42 h. The mixture is concentrated in vacuo and the residue chromatographed to yield the title compound, 79 mg (15%), as a tan solid.

Workup

concentrationThe mixture is concentrated in vacuo
customthe residue chromatographed

Sources & evidence

ORD record: ord-1f71017f179349fd95bf52de87aca6aa
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087626B2

Reaction notes

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