1-(tert-Butoxycarbonyl)-2-pyrroleboronic Acid → HCID 25066207, compound

HRID 555256Notes

Reaction equation

HRID 555256 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([C:12](=[O:25])[C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)[CH:3]=1.C(OC([N:33]1[CH:37]=[CH:36][CH:35]=[C:34]1B(O)O)=O)(C)(C)C>>[NH:33]1[CH:37]=[CH:36][CH:35]=[C:34]1[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([C:12](=[O:25])[C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)[CH:3]=1

Participants

3

Reactant 2

HCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 46929850HCID 46929850, compound

Product 1

HCID 25066207HCID 25066207, compound

Procedure

In the same manner as in the synthesis of Compound 457, Compound 19 shown in Reaction 5 and (1-(tert-butoxycarbonyl)-1H-pyrrole-2-yl)boronic acid were subjected to the Suzuki reaction to obtain N-(4-(1H-pyrrole-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide. Thus obtained N-(4-(1H-pyrrole-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide (20 mg, 0.05 mmol) was dissolved in methanol (3 ml), and NaOMe (30 μl, 0.5 mmol, 1.0 M/tetrahydrofuran) was added thereto at room temperature. The mixture was refluxed with stirring for 3 hours at 80° C. After completion of the reaction, the reaction mixture was cooled to room temperature, and diluted with an EtOAc solution. The organic layer was washed with water, and brine. The extracted organic layer was dried over anhydrous MgSO4, and the solid substance was filtered off. The filtrate was vacuum concentrated. The resulting residue was purified by column chromatography (SiO2, n-Hex/EA=2/1→1/2) to obtain Compound 597 (8 mg, 45%) in a form of a yellow solid.

Workup

  1. customwere subjected to the Suzuki reaction

Sources & evidence

ORD record
ord-7e516193f9ea4ff8a1f93b38c6b9fe33
Source dataset
uspto-grants-2011_11
Patent number
US08053439B2

Reaction notes

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