N-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide → HCID 25069767, compound

HRID 1035616Notes

Reaction equation

HRID 1035616 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:19].CC1(C)C(C)(C)OB([C:28]2[CH:29]=[C:30]([NH:34][C:35](=[O:37])[CH3:36])[CH:31]=[CH:32][CH:33]=2)O1>>[OH:19][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=3)[CH:7]=2)[C:2]=1[C:28]1[CH:29]=[C:30]([NH:34][C:35](=[O:37])[CH3:36])[CH:31]=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 2773989N-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamideHCID 24950391HCID 24950391, compound

Product 1

HCID 25069767HCID 25069767, compoundYield 77%

Procedure

The compound is prepared by the reaction of 1-bromo-6-(3-hydroxyphenyl)naphthalene-2-ol (150 mg, 0.48 mmol, 1 eq) with N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide (124.3 mg, 0.48 mmol, 1 eq) according to method A in 2 h. Purification by column chromatography with hexane/ethyl acetate 8/2 yields the desired compound in a yield of 77%, 136 mg.

Workup

  1. customPurification by column chromatography with hexane/ethyl acetate 8/2

Sources & evidence

ORD record
ord-5c2b1db58753416eb9b6b634ea77059d
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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