Sodium hydride → Ethyl 4-(2-methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindol-11-yl)-3-butenoate

HRID 433063Notes

Reaction equation

HRID 433063 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]3[CH2:11][C:12]4[C:17]([C:9]3=[C:8]([CH:18]=O)[C:7]=2[N:20]=1)=[CH:16][CH:15]=[CH:14][CH:13]=4.[H-].[Na+].C(OP([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])(OCC)=O)C>C1COCC1>[CH2:36]([O:35][C:33](=[O:34])[CH2:32][CH:31]=[CH:18][C:8]1[C:7]2[N:20]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[N:10]2[CH2:11][C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]=12)[CH3:37]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 281204Ethyl 3-(diethoxyphosphoryl)propanoateHCID 187582162-Methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindole-11-carbaldehyde

Product 1

HCID 69419312Ethyl 4-(2-methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindol-11-yl)-3-butenoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10.7 mmol of the compound obtained in Step E of Preparation 1 in 20 ml of anhydrous THF are placed in the presence of 1.2 eq of NaH (60% in oil) in 25 ml of anhydrous THF and of 1.2 eq of ethyl 3-(diethoxyphosphoryl)propanoate. The title compound is obtained after 3 hours' stirring at room temperature and gentle refluxing overnight.

Sources & evidence

ORD record
ord-162e7717db08414da36c527952e4bc34
Source dataset
uspto-grants-2003_12
Patent number
US06667304B2

Reaction notes

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