Indole → HCID 54470473, compound

HRID 1292257Notes

Reaction equation

HRID 1292257 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[CH:28]=[CH:27][C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:20]=4)=[CH:14][CH:15]=3)[C:10]([CH2:29][CH2:30][O:31][N:32]=[CH:33][C:34]([OH:36])=[O:35])=[C:9]2[CH3:37])[CH:2]=1.FC(F)(F)C(O)=O.[NH:45]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51]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[CH:28]=[CH:27][C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:20]=4)=[CH:14][CH:15]=3)[C:10]([CH2:29][CH2:30][O:31][N:32]=[CH:33][C:34]([OH:36])=[O:35])=[C:9]2[CH3:37])[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[CH:28]=[CH:27][C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:20]=4)=[CH:14][CH:15]=3)[C:10]([CH2:29][CH2:30][O:31][N:32]=[CH:33][C:34]([O:36][C:48]3[CH:53]=[N:45][CH:51]=[CH:50][CH:49]=3)=[O:35])=[C:9]2[CH3:37])[CH:2]=1

Participants

7

Reactant 5

HCID 798IndoleHCID 6422Trifluoroacetic acidHCID 183583-(Chloromethyl)pyridineHCID 24758Sodium hydrideHCID 54470473HCID 54470473, compound

Product 2

HCID 54470473HCID 54470473, compoundHCID 86752628HCID 86752628, compound

Procedure

The title compound is prepared by reaction of glyoxylic acid-O-2-[1-(3-pyridylmethyl)-5-(quinol-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-(quinol-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-97e2932121144e8c9458b523e1f85488
Source dataset
uspto-grants-1998_05
Patent number
US05756531

Reaction notes

Loading…