2-Bromopyridine → HCID 9882417, compound

HRID 1723887Notes

Reaction equation

HRID 1723887 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.CO[C:15](=[O:29])[CH2:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:20]1>C(Cl)Cl>[CH2:25]([CH:22]1[CH2:21][CH2:20][N:19]([CH2:18][CH2:17][CH2:16][C:15]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[O:29])[CH2:24][CH2:23]1)[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 9899559HCID 9899559, compoundHCID 178418339Butyllithium

Product 1

HCID 9882417HCID 9882417, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a dry 25 mL reaction flask was added 2-bromopyridine (200 mg, 1.3 mmol) dissolved in CH2Cl2 (3 mL) and the temperature was adjusted to −78° C. After being stirred for 20 min, addition of n-BuLi (0.84 mL, 1.4 mmol) was conducted under inert atmosphere. After additional 30 min, a solution of 23 dissolved in CH2Cl2 (2 mL) was added. The reaction mixture was left to warm to rt over-night before being quenched with H2SO4 (5 mL, 1 M). The reaction mixture was extracted with ethyl acetate (6×25 mL) and the combined organic phases were dried (MgSO4) and evaporated to dryness, to produce 0.31 g of crude 24. The crude product was subjected to CC [eluent: CH2Cl2: MEOH (10:1)] to give pure 24 (75 mg, 12%). LC-MS [M+H]+ 288 (cald. 288.2).

Workup

  1. customTo a dry 25 mL reaction flask
  2. customwas adjusted to −78° C
  3. waitAfter additional 30 min
  4. additionwas added
  5. waitThe reaction mixture was left
  6. custombefore being quenched with H2SO4 (5 mL, 1 M)
  7. extractionThe reaction mixture was extracted with ethyl acetate (6×25 mL)
  8. dry with materialthe combined organic phases were dried (MgSO4)
  9. customevaporated to dryness
  10. customto produce 0.31 g of crude 24

Sources & evidence

ORD record
ord-ace223dbdb064dac8202d0c4a570b7e0
Source dataset
uspto-grants-2009_02
Patent number
US07485651B2

Reaction notes

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