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

HRID 414918Notes

Reaction equation

HRID 414918 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].[CH2:22]([O:21][C:19](=[O:20])[CH2:18][N:13]1[CH:14]=[C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)[CH:10]=[CH:11][C:12]1=[NH:15])[CH3:23]

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 forms, and is recovered by filtration, washed with diethyl ether and then with ethanol, and oven-dried under reduced pressure. 8.78 g of compound are obtained.

Workup

  1. filtrationA precipitate forms, and is recovered by filtration
  2. washwashed with diethyl ether
  3. dry with materialwith ethanol, and oven-dried under reduced pressure

Sources & evidence

ORD record
ord-72087acc94554557a02d2567ad82e1f6
Source dataset
uspto-grants-2012_01
Patent number
US08088765B2

Reaction notes

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