Benzo(B)Thiophene-2-Boronic Acid → HCID 70664652, compound

HRID 1403349Notes

Reaction equation

[S:1]1[C:5](B(O)O)=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.Cl[C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:23]=1[N:24]([CH:26]([CH3:28])[CH3:27])[CH3:25])[CH:20]=[C:19]([C:29]([O:31][CH3:32])=[O:30])[CH:18]=[CH:17]2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:1]1[C:5]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][C:23]=2[N:24]([CH:26]([CH3:28])[CH3:27])[CH3:25])[CH:20]=[C:19]([C:29]([O:31][CH3:32])=[O:30])[CH:18]=[CH:17]3)=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of benzo[b]thiophen-2-ylboronic acid (180 mg, 1.01 mmol) in dioxane (6 mL) was added methyl 6-chloro-7-(isopropyl(methyl)amino)-2-naphthoate (120 mg, 0.41 mmol), K3PO4 (259 mg, 1.23 mmol), Pd(PPh3)4 (24.0 mg, 0.02 mmol) and water (3 drops) with stirring for 1 h at 90° C. in an oil bath with an inert atmosphere of nitrogen. The reaction mixture was concentrated under vacuum and then purified by a silica gel column with 1% to 4% ethyl acetate in petroleum ether to afford methyl 6-(benzo[b]thiophen-2-yl)-7-(isopropyl(methyl)amino)-2-naphthoate as a light yellow solid (140 mg, 87.5%).

Workup

concentrationThe reaction mixture was concentrated under vacuum
custompurified by a silica gel column with 1% to 4% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-1ef76f8f702b49718a3b0a75fafb1829
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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