Dimethyl methoxymethylenemalonate → HCID 71285326, compound

HRID 1481723Notes

Reaction equation

HRID 1481723 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[N:11]([CH3:35])[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([C:19](=[N:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1[O:33][CH3:34])[CH2:20][CH2:21][CH3:22])=[CH:14][CH:13]=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CO[CH:38]=[C:39]([C:44]([O:46]C)=O)[C:40]([O:42][CH3:43])=[O:41]>O(C1C=CC=CC=1)C1C=CC=CC=1>[Si:1]([O:8][CH2:9][C:10]1[N:11]([CH3:35])[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([C:19]1[N:23]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=3[O:33][CH3:34])[C:44](=[O:46])[C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:38][C:20]=1[CH2:21][CH3:22])=[CH:14][CH:13]=2)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 90770Dimethyl methoxymethylenemalonateHCID 89421765HCID 89421765, compound

Product 1

HCID 71285326HCID 71285326, compound

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
190 °C

Procedure

N-(1-(2-((tert-butyldimethylsilyloxy)methyl)-1-methyl-1H-indol-5-yl)butylidene)-1-(2,4-dimethoxyphenyl)methanamine (5.94 g, 12.0 mmol), prepared according to procedure described in Example 164 Step 1, was suspended in Ph2O (20 mL) then dimethyl 2-(methoxymethylene)malonate (3.55 g, 20.4 mmol, 1.7 eq) was added. The reaction mixture was heated to 190° C. for 1 h before mixture was cooled to room temperature then purified by flash column chromatography (0-50% EtOAc in CH2Cl2) to give the title compound. LC-MS 605.5 [M+H]+, RT 1.75 min.

Workup

  1. temperaturewas cooled to room temperature
  2. customthen purified by flash column chromatography (0-50% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-75f6b1832ac44475bb54f786924855c9
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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