4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → HCID 68731564, compound

HRID 455997Notes

Reaction equation

HRID 455997 reaction equation
[CH3:1][O:2][CH2:3][C:4]12[O:11][C:8]([CH2:12][O:13][CH3:14])([CH:9]=[CH:10]1)[CH2:7][C:6](OS(C(F)(F)F)(=O)=O)=[CH:5]2.CC1(C)C(C)(C)OB([C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)O1>CCOC(C)=O.C(Cl)Cl>[CH3:1][O:2][CH2:3][C:4]12[O:11][C:8]([CH2:12][O:13][CH3:14])([CH:9]=[CH:10]1)[CH2:7][C:6]([C:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=1)=[CH:5]2

Participants

4

Reactant 2

HCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 76587672HCID 76587672, compound

Product 1

HCID 68731564HCID 68731564, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

The title compound was prepared by the procedure of Example 4, step (b) using trifluoromethanesulfonic acid 1,5-bis-methoxymethyl-8-oxa-bicyclo[3.2.1]octa-2,6-dien-3-yl ester (as prepared in the previous step, 3.25 g, 9.45 mmol) and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (2.28 g, 10.4 mmol). Silica gel chromatography (5-10% EtOAc/DCM) afforded the title compound (2.19 g, 81%) as a light brown oil. Mass spectrum (ESI, m/z): Calcd. for C17H21NO3, 288.2 (M+H), found 288.2.

Workup

  1. customThe title compound was prepared by the procedure of Example 4, step (b)

Sources & evidence

ORD record
ord-ebd3bc1b6c0647a78647c931f086cf88
Source dataset
uspto-grants-2013_07
Patent number
US08497376B2

Reaction notes

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