Imidazole → HCID 11647526, compound

HRID 1042596Notes

Reaction equation

HRID 1042596 reaction equation
[N:1]1([C:6]2[O:10][C:9]3[C:11]([OH:17])=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:8]=3[C:7]=2[C:18](=[O:31])[C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=2)C=CN=[CH:2]1.[N:32]1C=CC=[CH:34][CH:33]=1.N1C=CC=N1.N1C=CN=C1>C(N(CC)CC)C.C1COCC1.C1(C)C=CC=CC=1>[N:1]1([C:6]2[O:10][C:9]3[C:11]([OH:17])=[C:12]([O:15][CH3:16])[CH:13]=[CH:14][C:8]=3[C:7]=2[C:18](=[O:31])[C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=2)[CH:2]=[CH:34][CH:33]=[N:32]1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 1048PyrazoleHCID 1049PyridineHCID 11510103HCID 11510103, compound

Product 1

HCID 11647526HCID 11647526, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

This material was prepared according to the procedure outlined above for 2-(N-imidazolyl)-7-hydroxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzo[b]furan (entry 27, Table 1), above, except pyridine was used as the solvent in place of toluene, THF and triethylamine and pyrazole was used as the nucleophile in place of imidazole. 1H NMR (300 MHz, CDCl3) δ 7.82 (d, 1H, J=2.55 Hz), 7.65 (d, 1H, J=1.51 Hz), 7.18 (d, 1H, J=8.57 Hz), 7.01 (s, 2H, benzoyl Hs), 6.96 (d, 1H, J=8.61 Hz), 6.30 (t, 1H, J=1.88 Hz), 3.96 (s, 3H, OMe), 3.86 (s, 3H, OMe), 3.75 (s, 6H, 2×OMe).

Workup

  1. customThis material was prepared

Sources & evidence

ORD record
ord-44f2ef16e595462dafe931dac0868256
Source dataset
uspto-grants-2013_10
Patent number
US08557982B2

Reaction notes

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