Dimethyl methoxymethylenemalonate → HCID 71284786, compound

HRID 1481727Notes

Reaction equation

HRID 1481727 reaction equation
[Si:1]([O:8][CH:9]1[C:13]2=[CH:14][C:15]3[CH:16]=[C:17]([C:21](=[N:25][CH2:26][C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=4[O:35][CH3:36])[CH2:22][CH2:23][CH3:24])[CH:18]=[CH:19][C:20]=3[N:12]2[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CO[CH:39]=[C:40]([C:45]([O:47]C)=O)[C:41]([O:43][CH3:44])=[O:42]>O(C1C=CC=CC=1)C1C=CC=CC=1>[Si:1]([O:8][CH:9]1[C:13]2=[CH:14][C:15]3[CH:16]=[C:17]([C:21]4[N:25]([CH2:26][C:27]5[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=5[O:35][CH3:36])[C:45](=[O:47])[C:40]([C:41]([O:43][CH3:44])=[O:42])=[CH:39][C:22]=4[CH2:23][CH3:24])[CH:18]=[CH:19][C:20]=3[N:12]2[CH2:11][CH2:10]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 90770Dimethyl methoxymethylenemalonateHCID 89423057HCID 89423057, compound

Product 1

HCID 71284786HCID 71284786, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A solution of 4 N-(1-(1-(tert-butyldimethylsilyloxy)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)butylidene)-1-(2,4-dimethoxyphenyl)methanamine (5.7 g, 11.2 mmol) and dimethyl 2-(methoxymethylene)malonate (2.55 g. 14.4 mmol) in Ph2O (10 mL) was heated at 220° C. for 30 min. The reaction mixture was then cooled to room temperature and loaded directly on silica gel eluting with hexanes/EtOAc (9:1) to afford the title compound as an orange foam (1.7 g, 25%).

Sources & evidence

ORD record
ord-59efb4b38b134c63b9ec8d9a960ef55c
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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