Benzofuran-4-yl trifluoromethanesulfonate → [3-Benzofuran-4-yl-5-(2-methoxy-pyridine-4-carbonyl)-phenyl]-carbamic acid methyl ester

HRID 1784864Notes

Reaction equation

HRID 1784864 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9](OS(C(F)(F)F)(=O)=O)[C:4]=2[CH:3]=[CH:2]1.CC1(C)C(C)(C)OB(C2C3C=COC=3C=CC=2)O1.[CH3:36][O:37][C:38](=[O:57])[NH:39][C:40]1[CH:45]=[C:44]([C:46]([C:48]2[CH:53]=[CH:52][N:51]=[C:50]([O:54][CH3:55])[CH:49]=2)=[O:47])[CH:43]=[C:42](Br)[CH:41]=1>>[CH3:36][O:37][C:38](=[O:57])[NH:39][C:40]1[CH:45]=[C:44]([C:46]([C:48]2[CH:53]=[CH:52][N:51]=[C:50]([O:54][CH3:55])[CH:49]=2)=[O:47])[CH:43]=[CH:42][C:41]=1[C:9]1[C:4]2[CH:3]=[CH:2][O:1][C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 21838291Benzofuran-4-yl trifluoromethanesulfonateHCID 574709912-(Benzofuran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane2×HCID 68847168[3-Bromo-5-(2-methoxy-pyridine-4-carbonyl)-phenyl]-carbamic acid methyl ester

Product 1

HCID 68843856[3-Benzofuran-4-yl-5-(2-methoxy-pyridine-4-carbonyl)-phenyl]-carbamic acid methyl ester

Procedure

Trifluoro-methanesulfonic acid benzofuran-4-yl ester was converted to 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzofuran using conditions described in Wang, Y.-C. and Georghiou, P. E., Org. Lett. 4: 2675-78 (2002). The Suzuki coupling of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzofuran to [3-bromo-5-(2-methoxy-pyridine-4-carbonyl)-phenyl]-carbamic acid methyl ester was carried out as described in Example 75 to give [3-benzofuran-4-yl-5-(2-methoxy-pyridine-4-carbonyl)-phenyl]-carbamic acid methyl ester. 1H NMR (400 MHz, CDCl3): δ 9.08 (s, 1H), 8.38 (dd, J=5.2, 0.5 Hz, 1H), 8.29 (t, J=1.6 Hz, 1H), 8.06 (t, J=1.7 Hz, 1H), 7.96 (d, J=2.1 Hz, 1H), 7.75 (t, J=1.6 Hz, 1H), 7.62-7.56 (m, 1H), 7.48-7.42 (m, 2H), 7.29 (dd, J=5.2, 1.3 Hz, 1H), 7.15 (dd, J=2.1, 1.0 Hz, 1H), 7.08 (s, 1H), 3.96 (s, 3H), 3.75 (s, 3H).

Sources & evidence

ORD record
ord-102fc239cdc54307991e1b80dd3df6e3
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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