Indole → HCID 86752624, compound

HRID 1292255Notes

Reaction equation

HRID 1292255 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][CH:21]=[CH:22][N:23]=4)=[CH:14][CH:15]=3)[C:10]([CH2:24][CH2:25][O:26][N:27]=[CH:28][C:29]([OH:31])=[O:30])=[C:9]2[CH3:32])[CH:2]=1.FC(F)(F)C(O)=O.[NH:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46]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][CH:21]=[CH:22][N:23]=4)=[CH:14][CH:15]=3)[C:10]([CH2:24][CH2:25][O:26][N:27]=[CH:28][C:29]([OH:31])=[O:30])=[C:9]2[CH3:32])[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][CH:21]=[CH:22][N:23]=4)=[CH:14][CH:15]=3)[C:10]([CH2:24][CH2:25][O:26][N:27]=[CH:28][C:29]([O:31][C:43]3[CH:48]=[N:40][CH:46]=[CH:45][CH:44]=3)=[O:30])=[C:9]2[CH3:32])[CH:2]=1

Participants

7

Reactant 5

HCID 798IndoleHCID 6422Trifluoroacetic acidHCID 183583-(Chloromethyl)pyridineHCID 24758Sodium hydrideHCID 86752624HCID 86752624, compound

Product 2

HCID 86752624HCID 86752624, compoundHCID 86752625HCID 86752625, compound

Procedure

The title compound is prepared by reaction of glyoxylic acid-O-2-[1-(3-pyridylmethyl)-5-(thiazol-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-(thiazol-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-9b38ba44fae345fda221da9f8c8c24bc
Source dataset
uspto-grants-1998_05
Patent number
US05756531

Reaction notes

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