Ethyl isocyanate → 6-(3-Ethylureido)pyridine-3-boronic acid pinacol ester

HRID 2243039Notes

Reaction equation

HRID 2243039 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[N:13][CH:14]=2)[O:3]1.[CH2:17]([N:19]=[C:20]=[O:21])[CH3:18]>C(Cl)(Cl)Cl>[CH2:17]([NH:19][C:20]([NH:15][C:12]1[CH:11]=[CH:10][C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:14][N:13]=1)=[O:21])[CH3:18]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Product 1

HCID 592084346-(3-Ethylureido)pyridine-3-boronic acid pinacol esterYield 76.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (1 g, 4.5 mmol) in chloroform (5 mL), ethyl isocyanate (0.33 mL, 4.5 mmol) was added. The resulting mixture was microwaved at 110° C. for one hour and concentrated to give 1 g of product (white solid). MS (ESP): 292 (M+H+) for C14H22BN3O3; NMR (CDCl3): 1.22 (t, 3H), 1.32 (s, 2H), 3.41 (m, 2H), 6.82 (d, 1H), 7.90 (dd, 1H), 8.52 (s, 1H), 8.62 (s, 1H), 9.40 (s, 1H).

Workup

  1. customThe resulting mixture was microwaved at 110° C. for one hour
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9f41173ed0b14e1f84273e49f42c5231
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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