Phosphorodichloridic acid, phenyl ester → Ethyl 4-chloro-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

HRID 733742

Reaction equation

HRID 733742 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:18]3[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][NH:15][C:14](=O)[C:13]=3[CH:12]=[CH:11]2)=[CH:5][CH:4]=1.P(Cl)([Cl:34])(OC1C=CC=CC=1)=O>>[Cl:34][C:14]1[C:13]2[CH:12]=[CH:11][N:10]([CH2:9][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:18]=2[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][N:15]=1

Participants

3

Reactant 2

HCID 13038Phosphorodichloridic acid, phenyl esterHCID 57840819Ethyl 1-{[4-(methyloxy)phenyl]methyl}-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

Product 1

HCID 57840887Ethyl 4-chloro-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

Procedure

Prepared in a similar manner to Example 243(e) using ethyl 1-{[4-(methyloxy)phenyl]methyl}-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (14.45 g) and phenyl dichlorophosphate (100 ml) to afford the title compound as a yellow oil (7.2 g).

Workup

  1. customPrepared in a similar manner to Example 243(e)

Sources & evidence

ORD record
ord-e85f43810b5b43549820003a70ed2893
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Linked notes

Loading…