2-Bromoacetamidopyridine → 2-Chloro-1-(2-oxo-2-(2-pyridyl)ethyl)naphtho[2,3-d]imidazole

HRID 2351300Notes

Reaction equation

[Cl:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]3[C:13](=[CH:14][C:4]=2[N:3]=1)[CH:12]=[CH:11][CH:10]=[CH:9]3.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)=[O:18]>>[Cl:1][C:2]1[N:3]([CH2:16][C:17](=[O:18])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[C:4]2[CH:14]=[C:13]3[C:8](=[CH:7][C:5]=2[N:6]=1)[CH:9]=[CH:10][CH:11]=[CH:12]3

Participants

Reactant 2

HCID 383842-Bromoacetamidopyridine

HCID 198461182-Chloro-1H-naphtho[2,3-d]imidazole

Product 1

HCID 198461332-Chloro-1-(2-oxo-2-(2-pyridyl)ethyl)naphtho[2,3-d]imidazoleYield 75.6%

Procedure

In a manner analogous to Example 28 steps a)→d) 2-chloro-1H-naphtho[2,3-d]imidazole (7.5 g) was reacted with 2-bromoacetylpyridine (8.7 g) to give 2-chloro-1-(2-oxo-2-(2-pyridyl)ethyl)naphtho[2,3-d]imidazole (9 g). This was reacted with thiourea (5.5 g) then NH4OH solution (100 ml) to give 2-mercapto-1-(2-oxo-2-(2-pyridyl)ethyl)naphtho[2,3-d]imidazole which compound was reduced with NaBH4 to give 2-mercapto-1-(2-hydroxy-2-(2-pyridyl)ethyl)naphtho[2,3-a]imidazole (1.3 g). Treatment of this with polyphosphoric acid (23 g) gave the title compound (0.75 g.) mp 197.5°-198.5° C.

Sources & evidence

ORD record: ord-f932ad0d61e34f4e89ac6bdf5c39c2b3
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04873237

Reaction notes

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