Sodium triacetoxyborohydride → Benzyl-[1-(5-bromo-pyridin-2-yl)-2,2,2-trifluoro-ethyl]-amine

HRID 525562Notes

Reaction equation

HRID 525562 reaction equation
[CH2:1](/[N:8]=[C:9](\[C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=1)/[C:10]([F:13])([F:12])[F:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.O>[CH2:1]([NH:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=1)[C:10]([F:13])([F:11])[F:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 178506344HCID 178506344, compound

Product 1

HCID 86695446Benzyl-[1-(5-bromo-pyridin-2-yl)-2,2,2-trifluoro-ethyl]-amineYield 33.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of Benzyl-[1-(5-bromo-pyridin-2-yl)-2,2,2-trifluoro-eth-(E)-ylidene]-amine (0.45 g, 1.31 mmol) in methanol (20 mL) is added sodium triacetoxy borohydride (0.55 g, 2.62 mmol) at 0° C. then stir at room temperature for 3 hours. Reaction mixture is diluted with water and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and purified by column chromatography eluting in 10% ethyl acetate in hexane to afford the title compound (0.15 g). 1H NMR (400 MHz, DMSO-d6) δ: 3.57-3.61 (m, 1H), 3.64-3.73 (m, 2H), 4.50 (m, 1H), 7.22-7.25 (m, 1H), 7.28-7.29 (m, 4H), 7.73 (d, J=8.2 Hz, 1H), 7.91-7.93 (dd, J1=8.2 Hz, J2=2.24 Hz, 1H), 8.48 (d, J=2.08 Hz, 1H). LC-MS (m/z): [M+H]=347.0.

Workup

  1. customReaction mixture
  2. extractionextracted with ethyl acetate
  3. dry with materialOrganic layer is dried over sodium sulphate, solvent
  4. customis evaporated in vacuo
  5. custompurified by column chromatography
  6. washeluting in 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-13dfdfb1a5824d9e8d43b1bff225d53d
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

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