Diisopropylethylamine → HCID 67972005, compound

HRID 1804616Notes

Reaction equation

HRID 1804616 reaction equation
[Br:1][C:2]1[C:3]([CH:8]=O)=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)C(C)C)(C)C.[N:19]1([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Br:1][C:2]1[C:3]([CH2:8][N:22]2[CH2:21][CH2:20][N:19]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 164142313-Bromopyridine-2-carbaldehyde

Product 1

HCID 67972005HCID 67972005, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 0.10 g (0.54 mmol) of 3-bromopyridine-2-carbaldehyde in 10 mL of dichloromethane was added activated powdered 4 Å molecular sieves, 0.20 mL (1.1 mmol) of N,N-diisopropylethylamine and 0.10 g (0.54 mmol) of tert-butyl piperazine-1-carboxylate. The resulting solution was stirred at ambient temperature for 1 h, then 0.34 g (1.6 mmol) of solid sodium triacetoxyborohydride was added in one portion. The heterogeneous reaction was allowed to stir at ambient temperature overnight and was then filtered through a pad of Celite®. The pad was washed with dichloromethane and the combined filtrates were washed with brine, dried over magnesium sulfate, filtered, and evaporated to dryness in vacuo. The residue was purified by silica gel chromatography eluting with a 0-100% ethyl acetate in hexanes gradient to afford the title compound as a colorless gum (0.055 g, 29%). LC-MS: m/z (ES) 356.2, 358.2 (MH)+.

Workup

  1. additionwas added
  2. customThe heterogeneous reaction
  3. stirringto stir at ambient temperature overnight
  4. filtrationwas then filtered through a pad of Celite®
  5. washThe pad was washed with dichloromethane
  6. washthe combined filtrates were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness in vacuo
  10. customThe residue was purified by silica gel chromatography
  11. washeluting with a 0-100% ethyl acetate in hexanes gradient

Sources & evidence

ORD record
ord-4e5ab13cd12b4a748161a194fbf03a1e
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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