Indole → HCID 86752626, compound

HRID 1292256Notes

Reaction equation

HRID 1292256 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]4[S:20][C:21]5[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=5[N:23]=4)=[CH:14][CH:15]=3)[C:10]([CH2:28][CH2:29][O:30][N:31]=[CH:32][C:33]([OH:35])=[O:34])=[C:9]2[CH3:36])[CH:2]=1.FC(F)(F)C(O)=O.[NH:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50]C=2)C=C1.N1C=CC=C(CCl)C=1.[H-].[Na+]>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]4[S:20][C:21]5[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=5[N:23]=4)=[CH:14][CH:15]=3)[C:10]([CH2:28][CH2:29][O:30][N:31]=[CH:32][C:33]([OH:35])=[O:34])=[C:9]2[CH3:36])[CH:2]=1.[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]4[S:20][C:21]5[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=5[N:23]=4)=[CH:14][CH:15]=3)[C:10]([CH2:28][CH2:29][O:30][N:31]=[CH:32][C:33]([O:35][C:47]3[CH:52]=[N:44][CH:50]=[CH:49][CH:48]=3)=[O:34])=[C:9]2[CH3:36])[CH:2]=1

Participants

7

Reactant 5

HCID 798IndoleHCID 6422Trifluoroacetic acidHCID 183583-(Chloromethyl)pyridineHCID 24758Sodium hydrideHCID 86752626HCID 86752626, compound

Product 2

HCID 86752626HCID 86752626, compoundHCID 86752627HCID 86752627, compound

Procedure

The title compound is prepared by reaction of glyoxylic acid-O-2-[1-(3-pyridylmethyl)-5-(benzothiazol-2-ylmethoxy)-2-methylindol-3-yl]ethyl oxime with trifluoroacetic acid to remove the t-BOC group followed by reaction of the indole intermediate with two equivalents of 3-pyridylmethyl chloride in the presence of a suitable base such as NaH to provide the intermediate glyoxylic acid 3-pyridyl ester-O-2-[1-(3-pyridylmethyl)-5-(benzothiazol-2-ylmethoxy)-2-methylindol-3-yl]ethyl oxime which is subsequently saponified.

Workup

  1. customto remove the t-BOC group

Sources & evidence

ORD record
ord-c56c829c78f444d08c79148659f61b94
Source dataset
uspto-grants-1998_05
Patent number
US05756531

Reaction notes

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