Water → HCID 58015548, compound

HRID 422091Notes

Reaction equation

HRID 422091 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1.[Br:10][C:11]1[O:19][C:18]2[CH:17]=[CH:16][N:15]([C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][N:24]=[CH:23]4)[C:14](=[O:29])[C:13]=2[CH:12]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CS(C)=O>[Br:10][C:11]1[O:19][C:18]2[CH:17]=[CH:16][N:15]([C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[N:25]([CH2:3][CH2:4][N:5]3[CH2:9][CH2:8][CH2:7][CH2:6]3)[N:24]=[CH:23]4)[C:14](=[O:29])[C:13]=2[CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 58015551HCID 58015551, compound

Product 1

HCID 58015548HCID 58015548, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
25 °C

Procedure

1-(2-Chloroethyl)pyrrolidine hydrochloride (213 mg, 1.25 mmol) was added to a suspension of 2-bromo-5-(1H-indazol-5-yl)furo[3,2-c]pyridin-4(5H)-one (187 mg, 0.570 mmol) and Cs2CO3 (1.11 g, 3.42 mmol) in anhydrous DMSO (3 mL) and the resulting suspension was stirred at 25° C. for 14 h. H2O (10 mL) was added and the aqueous suspension was filtered. The solid was dried under reduced pressure. Flash chromatography on silica gel [4.75:4.75:0.5 MTBE/CH2Cl2/(9:1 EtOH/NH4OH)] afforded the title compound (113 mg, 47%) as a light yellow powder with data matching those reported in Example 9.

Workup

  1. filtrationthe aqueous suspension was filtered
  2. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-5bc9c70bca6848f4b1b6c2bf77519bff
Source dataset
uspto-grants-2012_01
Patent number
US08101632B2

Reaction notes

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