4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane → Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-(prop-1-en-2-yl)pyrazine-2-carboxylate

HRID 2368228Notes

Reaction equation

HRID 2368228 reaction equation
[C:1]([O:5][C:6]([N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:9]1[C:10]([C:16]([O:18][CH3:19])=[O:17])=[N:11][C:12](Br)=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:27](B1OC(C)(C)C(C)(C)O1)([CH3:29])=[CH2:28]>>[C:1]([O:5][C:6]([N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:9]1[C:10]([C:16]([O:18][CH3:19])=[O:17])=[N:11][C:12]([C:27]([CH3:29])=[CH2:28])=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 86660188Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-bromopyrazine-2-carboxylate

Product 1

HCID 70097498Methyl 3-(bis(tert-butoxycarbonyl)amino)-6-(prop-1-en-2-yl)pyrazine-2-carboxylate

Procedure

The product was obtained starting from methyl 3-(bis(tert-butoxycarbonyl)amino)-6-bromopyrazine-2-carboxylate (1.13 g, 2.61 mmol) and 2-isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (672 μl, 3.4 mmol) according to the method described in example A-1, step 1 after extraction with ethyl acetate and purification by silica gel chromatography using a heptane/ethyl acetate gradient as yellow viscous oil (323 mg, 31%).

Workup

  1. customThe product was obtained
  2. extractionafter extraction
  3. customwith ethyl acetate and purification by silica gel chromatography

Sources & evidence

ORD record
ord-fc27564655614d60bf24d2876f6444da
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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