Sodium borohydride → HCID 119086991, compound

HRID 2207347Notes

Reaction equation

HRID 2207347 reaction equation
BrC1C=C(/C=C/C(OCC)=O)C=CC=1.[Br:15][C:16]1[CH:17]=[C:18](/[CH:22]=[CH:23]\[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:19]=[N:20][CH:21]=1.[BH4-].[Na+]>CO.O.C(OCC)(=O)C.[Cu]Cl>[Br:15][C:16]1[CH:17]=[C:18]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:19]=[N:20][CH:21]=1

Participants

8

Reactant 3

HCID 4311764Sodium borohydrideHCID 5369361Ethyl 3-(3-bromophenyl)acrylateHCID 119086990Ethyl (2Z)-3-(5-bromo-3-pyridinyl)-2-propenoate

Product 1

HCID 119086991HCID 119086991, compound

Reagents, catalysts & solvents 4

HCID 62652Cuprous chlorideCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl (2E)-3-(3-bromophenyl)prop-2-enoate and ethyl (2Z)-3-(5-bromopyridin-3-yl)prop-2-enoate (4:1 ratio of isomers, 332 mg, 1.30 mmol) in methanol (10 mL) and water (2.5 mL) was added copper (I) chloride (257 mg, 2.59 mmol) and sodium borohydride (98 mg, 2.59 mmol). After 15 minutes, the reaction was diluted with ethyl acetate and filtered through CELITE. The filtrate was washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to afford ethyl 3-(5-bromopyridin-3-yl)propanoate. MS ESI calc'd. for C10H13BrNO2 [M+H]+ 258 and 260. found 258 and 260. 1H NMR (500 MHz, DMSO-d6) δ 8.52 (d, J=2.2 Hz, 1H), 8.44 (d, J=1.8 Hz, 1H), 7.96 (t, J=2.0 Hz, 1H), 4.02 (q, J=7.1 Hz, 2H), 2.84 (t, J=7.5 Hz, 2H), 2.67 (t, J=7.5 Hz, 2H), 1.12 (t, J=7.1 Hz, 3H).

Workup

  1. filtrationfiltered through CELITE
  2. washThe filtrate was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-262386db314b44c3b8969070248ccce7
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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