Sodium hydride → HCID 67253812, compound

HRID 1798229Notes

Reaction equation

HRID 1798229 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:17])[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2].[H-].[Na+].Br[C:22]1[N:23]=[CH:24][C:25]([C:28]#[N:29])=[N:26][CH:27]=1>C1COCC1>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:22]3[CH:27]=[N:26][C:25]([C:28]#[N:29])=[CH:24][N:23]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 378187222-Bromo-5-cyanopyrazineHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 67253812HCID 67253812, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (3.68 g, 20.0 mmol) in THF (60 mL) was treated with NaH (1.20 g, 30.0 mmol) at 0° C. The resulting suspension was stirred at room temperature 15 min and 5-bromo-pyrazine-2-carbonitrile was added. The reaction was stirred at room temperature for 3 h. The suspension was quenched with 1N HCl and extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate=1:1) to afford the title compound (1.63 g). 1H NMR (300 MHz, CD3OD) δ 8.58 (s, 1H), 8.55 (s, 1H), 7.29 (s, 1H), 7.16 (s, 1H), 5.73-5.69 (m, 1H), 4.16 (q, 2H), 3.27-3.18 (m, 1H), 2.56-2.48 (m, 1H), 2.41 (s, 3H), 1.23 (t, 3H). MS found: (M+H)+=354.1.

Workup

  1. stirringThe reaction was stirred at room temperature for 3 h
  2. customThe suspension was quenched with 1N HCl
  3. extractionextracted with ethyl acetate
  4. customThe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ce7fc7c0d6844246be8df2542ef06f2b
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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