N-Methyldiethanolamine → 2-(5-Bromo-3-pyridinyl)tetrahydro-6-methyl-4H-1,3,6,2-dioxazaborocine

HRID 1989240Notes

Reaction equation

HRID 1989240 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([B:8]([OH:10])[OH:9])[CH:7]=1.[CH3:11][N:12]([CH2:16][CH2:17]O)[CH2:13][CH2:14]O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([B:8]2[O:10][CH2:17][CH2:16][N:12]([CH3:11])[CH2:13][CH2:14][O:9]2)[CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 7767N-MethyldiethanolamineHCID 38148115-Bromopyridine-3-boronic acid

Product 1

HCID 574688192-(5-Bromo-3-pyridinyl)tetrahydro-6-methyl-4H-1,3,6,2-dioxazaborocineYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
23 °C

Procedure

Step 1) A mixture of 3-bromopyridine-5-boronic acid [CAS-no. 452972-09-7] (10 g, 50 mmol) and N-methyldiethanolamine (5.9 g, 50 mmol) in toluene (50 mL) was stirred at 23° C. for 24 h, then totally evaporated, triturated with heptane to give 2-(5-bromo-pyridin-3-yl)-6-methyl-[1,3,6,2]dioxazaborocane (14.1 g, 100%) as an off-white solid. MS (ISP) 285.0 [(M+H)+].

Workup

  1. customtotally evaporated
  2. customtriturated with heptane

Sources & evidence

ORD record
ord-e596949da273462fa0bf77256bb12c21
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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