Methyl iodide → benzyl 2,4-bis(benzyloxy)-5-methoxy-6-(1-methyl-1H-indol-5-yl)nicotinate

HRID 1481787Notes

Reaction equation

HRID 1481787 reaction equation
[CH2:1]([O:8][C:9]1[N:24]=[C:23]([C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[N:30]([CH3:34])[CH:29]=[CH:28]3)[C:22]([OH:35])=[C:21]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:47]>CN(C=O)C>[CH2:1]([O:8][C:9]1[N:24]=[C:23]([C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[N:30]([CH3:34])[CH:29]=[CH:28]3)[C:22]([O:35][CH3:47])=[C:21]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71284878HCID 71284878, compound

Product 1

HCID 71284261benzyl 2,4-bis(benzyloxy)-5-methoxy-6-(1-methyl-1H-indol-5-yl)nicotinateYield 89.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a solution of benzyl 2,4-bis(benzyloxy)-5-hydroxy-6-(1-methyl-1H-indol-5-yl)nicotinate (80 mg, 0.14 mmol) in DMF (0.3 mL) was added 60% NaH (7.3 mg, 0.18 mmol). After 15 min, iodomethane (13 μL, 0.20 mmol) was added. The mixture was stirred at room temperature for another 30 min and then loaded directly onto a silica column and chromatographed to give benzyl 2,4-bis(benzyloxy)-5-methoxy-6-(1-methyl-1H-indol-5-yl)nicotinate (73 mg, 89%).

Workup

  1. customchromatographed

Sources & evidence

ORD record
ord-e1d5a583df7146a28c4975c0995857c9
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

Loading…