Ethyl bromoacetate → Ethyl [2-imino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyridin-1-yl]acetate hydrobromide

HRID 1684926Notes

Reaction equation

HRID 1684926 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.[Br:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>>[BrH:17].[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[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

3

Reactant 2

HCID 7748Ethyl bromoacetateHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Product 1

HCID 86761542Ethyl [2-imino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-pyridin-1-yl]acetate hydrobromide

Procedure

5.0 g of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ylamine in 7.6 ml of ethyl 2-bromoacetate are placed in a round-bottomed flask and the mixture is stirred at ambient temperature for 20 h. A precipitate is formed and is collected by filtration, washed with diethyl ether and then with ethanol and dried in an oven under reduced pressure. 8.78 g of compound are obtained.

Workup

  1. customA precipitate is formed
  2. filtrationis collected by filtration
  3. washwashed with diethyl ether
  4. dry with materialwith ethanol and dried in an oven under reduced pressure

Sources & evidence

ORD record
ord-59d1ccb6eed14e17b706fc0dc1ba0330
Source dataset
uspto-grants-2012_04
Patent number
US08148370B2

Reaction notes

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