Benzene, 1-(bromomethyl)-3-nitro- → 4-(3,5-Dichloropyridin-4-ylamino)-7-methoxy-8-(3-nitrobenzyloxy)-2H-chromen-2-one

HRID 20658

Reaction equation

HRID 20658 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Cl:34])[C:18]=1[NH:19][C:20]1[C:29]2[C:24](=[C:25]([OH:32])[C:26]([O:30][CH3:31])=[CH:27][CH:28]=2)[O:23][C:22](=[O:33])[CH:21]=1>>[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Cl:34])[C:18]=1[NH:19][C:20]1[C:29]2[C:24](=[C:25]([O:32][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=3)[C:26]([O:30][CH3:31])=[CH:27][CH:28]=2)[O:23][C:22](=[O:33])[CH:21]=1

Participants

3

Reactant 2

HCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 248495704-(3,5-dichloropyridin-4-ylamino)-8-hydroxy-7-methoxy-2H-chromen-2-one

Product 1

HCID 248496204-(3,5-Dichloropyridin-4-ylamino)-7-methoxy-8-(3-nitrobenzyloxy)-2H-chromen-2-one

Procedure

The title compound was prepared from 1-(bromomethyl)-3-nitrobenzene and 4-(3,5-dichloropyridin-4-ylamino)-8-hydroxy-7-methoxy-2H-chromen-2-one (Example 29) following the procedure outlined in Example 25. 1H NMR (400 MHz, DMSO-d6): δ 9.55 (s, 1H), 8.81 (s, 2H), 8.40 (s, 1H), 8.19 (ddd, 1H), 7.99 (d, 1H), 7.95 (d, 1H), 7.68 (t, 1H), 7.24 (d, 1H), 5.20 (s, 2H), 4.65 (s, 1H), 3.94 (s, 3H); MS (ESI): 487.8.

Sources & evidence

ORD record
ord-b76a830f6999434d98f5b3cdcc7957fc
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Linked notes

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