m-(Dimethylamino)benzyl alcohol → HCID 71092852, compound

HRID 1430219Notes

Reaction equation

HRID 1430219 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:4]=[C:5]([CH2:9]O)[CH:6]=[CH:7][CH:8]=1.[CH3:12][C:13]1([CH3:25])[C:17]([CH3:19])([CH3:18])[O:16][B:15]([C:20]2[CH:21]=[N:22][NH:23][CH:24]=2)[O:14]1.C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:11])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][N:23]2[CH:24]=[C:20]([B:15]3[O:14][C:13]([CH3:25])([CH3:12])[C:17]([CH3:19])([CH3:18])[O:16]3)[CH:21]=[N:22]2)[CH:4]=1

Participants

5

Reactant 3

HCID 90133m-(Dimethylamino)benzyl alcoholHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 4622928Cyanomethylenetributylphosphorane

Product 1

HCID 71092852HCID 71092852, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (3-(dimethylamino)phenyl)methanol (0.100 g), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.167 g) and cyanomethylenetributylphosphorane (0.208 g) were added and stirred together in toluene (1 mL) at room temperature. After stirring overnight the reaction was loaded directly onto silica gel and eluted using a gradient of 5% to 35% ethyl acetate/hexanes to provide the title compound.

Workup

  1. washeluted

Sources & evidence

ORD record
ord-619dedc991cb444ab2eeafe4c4243d3b
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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