Ethyl Acetate → [2-(1-Benzyl-1H-pyrazol-4-yl)-7-hydroxy-6-methoxy-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)-methanone

HRID 2059602Notes

Reaction equation

HRID 2059602 reaction equation
C([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[C:11](I)[C:10]=1[OH:18])C1C=CC=CC=1.[CH2:19]([N:26]1[CH:30]=[C:29]([C:31]#[CH:32])[CH:28]=[N:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:33][O:34][C:35]1[CH:36]=[C:37](I)[CH:38]=[C:39]([O:43][CH3:44])[C:40]=1[O:41][CH3:42].[C:46](OCC)(=[O:48])C>CCCCCC>[CH2:19]([N:26]1[CH:30]=[C:29]([C:31]2[O:18][C:10]3[C:9]([OH:8])=[C:14]([O:15][CH3:16])[CH:13]=[CH:12][C:11]=3[C:32]=2[C:46]([C:37]2[CH:36]=[C:35]([O:34][CH3:33])[C:40]([O:41][CH3:42])=[C:39]([O:43][CH3:44])[CH:38]=2)=[O:48])[CH:28]=[N:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 2981335-Iodo-1,2,3-trimethoxybenzeneHCID 574219391-benzyl-4-ethynyl-1H-pyrazoleHCID 574219402-Benzyloxy-6-iodo-3-methoxy-phenol

Product 1

HCID 59576644[2-(1-Benzyl-1H-pyrazol-4-yl)-7-hydroxy-6-methoxy-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)-methanone

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Application of the general procedure to 2-benzyloxy-6-iodo-3-methoxy-phenol, 1-benzyl-4-ethynyl-1H-pyrazole and 3,4,5-trimethoxy-iodo-benzene (NB—the initial coupling proceeded slowly and was continued overnight) and silica-gel flash chromatography (eluent=40% ethyl acetate in hexane) gave a mixture of the title compound, [2-(1-benzyl-1-pyrazol-4-yl)-7-benzyloxy-6-methoxy-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)-methanone and the corresponding non-carbonyl inserted derivative. This mixture was again subjected to silica-gel flash chromatography (sequential elution—2% diethyl ether in DCM, 10%). Concentration of the first eluted fractions afforded a mixture of the 7-benzyloxy derivative and the non-carbonyl inserted material and was used in subsequent chemistry. The later fractions gave the title compound (2% yield) as a pale yellow solid. An analytical sample was obtained by recrystallisation from DCM and hexane. 1H-NMR (CDCl3) δ 8.08 (s, 1H), 8.03 (s, 1H), 7.36-7.27 (m, 3H), 7.22-7.19 (m, 2H), 7.10 (s, 2H), 6.80 (d, J=8.6 Hz, 1H), 6.74 (d, J=8.6 Hz, 1H), 5.28 (s, 2H), 3.92 (s, 3H), 3.91 (s, 3H), 3.74 (s, 6H).

Sources & evidence

ORD record
ord-47eed009e3c84848be640ba839cee05e
Source dataset
uspto-grants-2012_10
Patent number
US08278290B2

Reaction notes

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