Triethylamine → 3-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)aniline

HRID 723051Notes

Reaction equation

HRID 723051 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:9].CCN(CC)CC.[CH3:17][C:18]1([CH3:25])[C:22]([CH3:24])([CH3:23])[O:21][BH:20][O:19]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[CH3:8][C:7]1[C:2]([B:20]2[O:21][C:22]([CH3:24])([CH3:23])[C:18]([CH3:25])([CH3:17])[O:19]2)=[C:3]([NH2:9])[CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6037812-Bromo-3-methylanilineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolane

Product 1

HCID 218860963-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)anilineYield 40%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

The procedure described in Example 3: step b was followed using 2-bromo-3-methyl-phenylamine (185 mg, 1.0 mmol, Example 25: step a), PdCl2(PPh3)2 (70.2 mg, 0.1 mmol), dioxane (3 mL), and Et3N (729 μL, 6 mmol), 4,4,5,5,-tetramethyl-[1,3,2]-dioxaborolane (453 μL, 3 mmol). Purification by preparative SiO2 TLC (25% EtOAc in hexanes) of the residue yielded the title compound (94 mg, 40%) as a yellow solid. ESI-MS (m/z): Calcd. for C13H20BNO2: 234.1 (M+H) found: 234.1.

Workup

  1. customPurification by preparative SiO2 TLC (25% EtOAc in hexanes) of the residue

Sources & evidence

ORD record
ord-c92889de263c48c4951fcf2fd91f1d7c
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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