Potassium Carbonate → 6-Methoxy-2-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan

HRID 2059598Notes

Reaction equation

HRID 2059598 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].[C:11]([C:13]1[CH:14]=[N:15][N:16]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH:17]=1)#[CH:12].[CH3:27][O:28][C:29]1[CH:30]=[C:31](I)[CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36].[C:40](=O)([O-])[O-:41].[K+].[K+]>CO.C(OCC)(=O)C>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]2[C:12]([C:40](=[O:41])[C:31]3[CH:30]=[C:29]([O:28][CH3:27])[C:34]([O:35][CH3:36])=[C:33]([O:37][CH3:38])[CH:32]=3)=[C:11]([C:13]3[CH:14]=[N:15][N:16]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[CH:17]=3)[O:10][C:3]=2[CH:4]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2981335-Iodo-1,2,3-trimethoxybenzeneHCID 114140152-Iodo-5-methoxyphenolHCID 574219374-Ethynyl-1-(4-methoxybenzyl)-1H-pyrazole

Product 1

HCID 574219386-Methoxy-2-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared by application of the general procedure to 2-iodo-5-methoxy-phenol, 4-ethynyl-1-(4-methoxy-benzyl)-1H-pyrazole and 3,4,5-trimethoxy-iodo-benzene. The crude product was stirred with potassium carbonate (excess) in methanol for 3 h to hydrolyse ester by-products and submitted to silica-gel flash chromatography (eluent=2:1 hexanes: ethyl acetate) to afford a mixture of the title compound and the corresponding non-carbonyl inserted derivative. This mixture was used directly in the subsequent deprotection. An analytical sample was purified by recrystallisation from dichloromethane/hexane. 1H-NMR (CDCl3) δ 8.03 (s, 1H), 8.01 (s, 1H), 7.18 (d, J=8.6 Hz, 2H), 7.14 (d, J=8.7 Hz, 1H), 7.10 (s, 2H), 7.02 (d, J=2.2 Hz, 1H), 6.86 (d, J=8.6 Hz, 2H), 6.79 (dd, J=8.7, 2.2 Hz, 1H), 5.22 (s, 2H), 3.92 (s, 3H), 3.85 (s, 3H), 3.78 (s, 3H), 3.75 (s, 6H). 13C—NMR (CDCl3) δ 190.2, 159.5, 158.1, 154.2, 153.3, 152.9, 142.3, 139.1, 133.6, 129.8, 129.3, 127.6, 121.7, 120.9, 114.2, 113.8, 112.9, 112.2, 107.0, 95.5, 60.9, 56.1, 55.8, 55.6, 55.2.

Workup

  1. customto afford

Sources & evidence

ORD record
ord-3cf02b42caca43e995f03ed8f1fddb12
Source dataset
uspto-grants-2012_10
Patent number
US08278290B2

Reaction notes

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