Methyl N-methylindole-6-carboxylate → HCID 54440772, compound

HRID 1655052Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2[CH3:14])=[CH:7][CH:6]=1)=[O:4].[N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[CH2:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=1>O1CCOCC1.[Ag]=O>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH2:31][C:30]3[CH:29]=[CH:28][C:27]([O:26][CH2:25][C:16]4[CH:17]=[CH:18][C:19]5[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=5)[N:15]=4)=[CH:34][CH:33]=3)=[CH:10][N:11]2[CH3:14])=[CH:7][CH:6]=1)=[O:4]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 1-methylindole-6-carboxylic acid methyl ester (Example 10, part i) (1.5 g) and 4-(quinolin-2-ylmethoxy)benzyl chloride (2.43 g) in dioxan (15 ml), silver oxide (2 g) was added and the suspension heated at 70° C. overnight. The solvent was removed in vacuo, the residue ultrasonicated with ethylacetate and insoluble material removed by filtration through celite. The filtrate was evaporated to dryness and the residue purified by chromatography on flash silica, eluting with petroleum spirit 40°-60° C./diethyl ether (1:1) to give the product as a white solid. A small quantity was crystallised from petroleum spirit 40°-60° C./diethyl ether (1:1).

Workup

customThe solvent was removed in vacuo
customthe residue ultrasonicated with ethylacetate and insoluble material
customremoved by filtration through celite
customThe filtrate was evaporated to dryness
customthe residue purified by chromatography on flash silica
washeluting with petroleum spirit 40°-60° C./diethyl ether (1:1)

Sources & evidence

ORD record: ord-c47c8ba217624351af2e802d8d1a3195
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05410061

Reaction notes

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