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

HRID 1042566Notes

Reaction equation

HRID 1042566 reaction equation
C(OC1C(OC)=CC=C(I)C=1O)C1C=CC=CC=1.C(N1C=C(C#C)C=N1)C1C=CC=CC=1.COC1C=C(I)C=C(OC)C=1OC.[CH2:46]([N:53]1[CH:57]=[C:56]([C:58]2[O:59][C:60]3[C:80]([O:81]CC4C=CC=CC=4)=[C:79]([O:89][CH3:90])[CH:78]=[CH:77][C:61]=3[C:62]=2[C:63]([C:65]2[CH:70]=[C:69]([O:71][CH3:72])[C:68]([O:73][CH3:74])=[C:67]([O:75][CH3:76])[CH:66]=2)=[O:64])[CH:55]=[N:54]1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CCCCCC.C(OCC)(=O)C>[CH2:46]([N:53]1[CH:57]=[C:56]([C:58]2[O:59][C:60]3[C:80]([OH:81])=[C:79]([O:89][CH3:90])[CH:78]=[CH:77][C:61]=3[C:62]=2[C:63]([C:65]2[CH:66]=[C:67]([O:75][CH3:76])[C:68]([O:73][CH3:74])=[C:69]([O:71][CH3:72])[CH:70]=2)=[O:64])[CH:55]=[N:54]1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

7

Reactant 4

HCID 2981335-Iodo-1,2,3-trimethoxybenzeneHCID 574219391-benzyl-4-ethynyl-1H-pyrazoleHCID 574219402-Benzyloxy-6-iodo-3-methoxy-phenolHCID 57421941[2-(1-benzyl-1H-pyrazol-4-yl)-7-benzyloxy-6-methoxy-benzofuran-3-yl]-(3,4,5-trimethoxyphenyl)-methanone

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 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

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-1H-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-84b647227af741d783a7a61e68d07643
Source dataset
uspto-grants-2013_10
Patent number
US08557982B2

Reaction notes

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