Sodium hydride → (+/-)-trans-2-(2-Chloro-5-dimethylamino-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one

HRID 1363368Notes

Reaction equation

HRID 1363368 reaction equation
[OH:1][C:2]1[C:7]([C@@H:8]2[CH2:12][CH2:11][N:10]([CH3:13])[C@H:9]2[CH2:14][OH:15])=[C:6]([O:16][CH3:17])[CH:5]=[C:4]([O:18][CH3:19])[C:3]=1[C:20](=[O:22])[CH3:21].CO[C:25](=O)[C:26]1[CH:31]=[C:30]([N:32]([CH3:34])[CH3:33])[CH:29]=[CH:28][C:27]=1[Cl:35].[H-].[Na+]>CN(C=O)C>[Cl:35][C:27]1[CH:28]=[CH:29][C:30]([N:32]([CH3:34])[CH3:33])=[CH:31][C:26]=1[C:25]1[O:1][C:2]2[C:3]([C:20](=[O:22])[CH:21]=1)=[C:4]([O:18][CH3:19])[CH:5]=[C:6]([O:16][CH3:17])[C:7]=2[C@@H:8]1[CH2:12][CH2:11][N:10]([CH3:13])[C@H:9]1[CH2:14][OH:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 59318484(-)-trans-1-[2-Hydroxy-3-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-4,6-dimethoxyphenyl]-1-ethanoneHCID 66909163Methyl 2-chloro-5-(dimethylamino)benzoate

Product 1

HCID 131728661(+/-)-trans-2-(2-Chloro-5-dimethylamino-phenyl)-8-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-5,7-dimethoxy-chromen-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound of example 6 (0.8 g, 2.58 mmol) in dry DMF (15 mL) was reacted with methyl-2 chloro-5-dimethylaminobenzoate (1.65 g, 7.7 mmol) in the presence of NaH (50%, 0.62 g, 12.9 mmol) as described in example 16 to obtain the title compound.

Sources & evidence

ORD record
ord-e9b7b4b4c5ee4ceaa5f15741e96a832e
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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