Trimethyl methanetricarboxylate → HCID 71284275, compound

HRID 1481699Notes

Reaction equation

HRID 1481699 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[N:11]([CH3:28])[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([C:19](=[N:23]C(C)(C)C)[CH2:20][CH2:21][CH3:22])=[CH:14][CH:13]=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:29]([C:38](OC)=[O:39])([C:34](OC)=[O:35])[C:30]([O:32][CH3:33])=[O:31]>O(C1C=CC=CC=1)C1C=CC=CC=1>[Si:1]([O:8][CH2:9][C:10]1[N:11]([CH3:28])[C:12]2[C:17]([CH:18]=1)=[CH:16][C:15]([C:19]1[NH:23][C:34](=[O:35])[C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:38]([OH:39])[C:20]=1[CH2:21][CH3:22])=[CH:14][CH:13]=2)([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 136922Trimethyl methanetricarboxylateHCID 89422913HCID 89422913, compound

Product 1

HCID 71284275HCID 71284275, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
230 °C

Procedure

To a solution of N-(1-(2-((tert-butyldimethylsilyloxy)methyl)-1-methyl-1H-indol-5-yl)butylidene)-2-methylpropan-2-amine (2.10 g, ca. 5.2 mmol), prepared according to procedure described in Example 39 Step 5, in Ph2O (5 mL) was added trimethyl methanetricarboxylate (1.68 g, 8.8 mmol, 1.7 eq). The mixture was heated to 230° C. for 2 h. The mixture was cooled to room temperature then purified by flash column chromatography (0-50% EtOAc in CH2Cl2) to afford the title compound (0.51 g, 1.1 mmol, 21%) as a light yellow solid. LC-MS 469.2 [M−H]−, 471.2 [M+H]+, RT 1.67 min.

Workup

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

Sources & evidence

ORD record
ord-8d7f6a8e25984bd1bf885871f7a63c3c
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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