Cesium carbonate → HCID 25017297, compound

HRID 422088Notes

Reaction equation

HRID 422088 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:16][C:15]3[CH:14]=[CH:13][N:12]([C:17]4[CH:18]=[C:19]5[C:23](=[CH:24][CH:25]=4)[NH:22][N:21]=[CH:20]5)[C:11](=[O:26])[C:10]=3[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl.Cl[CH2:29][CH2:30][N:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.CN1C(=O)CCC1.O.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:16][C:15]3[CH:14]=[CH:13][N:12]([C:17]4[CH:18]=[C:19]5[C:23](=[CH:24][CH:25]=4)[N:22]([CH2:29][CH2:30][N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)[N:21]=[CH:20]5)[C:11](=[O:26])[C:10]=3[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 58015549HCID 58015549, compound

Product 1

HCID 25017297HCID 25017297, compoundYield 25%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 2-(3-chlorophenyl)-5-(1H-indazol-5-yl)furo[3,2-c]pyridin-4(5H)-one (0.365 g, 0.732 mmol) in DMSO (1.5 mL) and NMP (0.94 mL) was added (2-chloroethyl)pyrrolidine hydrochloride (0.273 g, 1.61 mmol) and Cs2CO3 (1.43 g, 4.39 mmol). The reaction mixture was stirred at ambient temperature for 18 h; then the reaction mixture was diluted with H2O (10 mL) and EtOAc (20 mL). The desired solids were collected by filtration. Purification by flash chromatography (silica gel, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 to 0:100) yielded the title compound (83.8 mg, 25%) as a light yellow solid: 1H NMR (500 MHz, CDCl3) δ 8.05 (s, 1H), 7.79 (t, J=2.0 Hz, 1H), 7.72 (d, J=1.5 Hz, 1H), 7.66 (d, J=7.5 Hz, 1H), 7.56 (d, J=9.0 Hz, 1H), 7.42 (dd, J=8.5, 2.0 Hz, 1H), 7.39-7.35 (m, 2H), 7.33-7.31 (m, 1H), 7.29 (s, 1H), 6.68 (d, J=7.5 Hz, 1H), 4.58 (t, J=7.5 Hz, 2H), 3.03 (t, J=7.0 Hz, 2H), 2.60 (m, 4H), 1.80 (m, 4H); ESI MS m/z 459 [M+H]+; HPLC (Method A) >99% (AUC), tR=16.7 min.

Workup

  1. filtrationThe desired solids were collected by filtration
  2. customPurification by flash chromatography (silica gel, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 to 0:100)

Sources & evidence

ORD record
ord-831326e0709e4cfe938128d12d3ad064
Source dataset
uspto-grants-2012_01
Patent number
US08101632B2

Reaction notes

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