2-Bromopyridine → HCID 19026970, compound

HRID 1032949Notes

Reaction equation

HRID 1032949 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.CCCCCC.[CH3:19][N:20]([CH3:33])[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[O:29][CH2:30][O:31][CH3:32])[CH:24]=[O:25].[Cl-].[NH4+]>O1CCCC1>[CH3:33][N:20]([CH3:19])[C:21]1[CH:22]=[C:23]([CH:24]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[OH:25])[CH:26]=[CH:27][C:28]=1[O:29][CH2:30][O:31][CH3:32]

Participants

7

Reactant 5

HCID 79732-BromopyridineHCID 8058HexaneHCID 25517Ammonium Chloride2×HCID 190269753-Dimethylamino-4-methoxymethoxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 19026970HCID 19026970, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-bromopyridine (3.05 g, 19.3 mmol) in dry tetrahydrofuran (100 ml) was added dropwise n-butyl lithium in hexane (1.6M, 12.0 ml, 19.2 mmol) under nitrogen atmosphere. After stirring at -78° C. for 30 minutes, thereto was added dropwise a solution of the aldehyde compound (Compound A) (3.00 g, 14.3 mmol) in dry tetrahydrofuran (20 ml), and the mixture was stirred at -78° C. for 2 hours. A saturated aqueous solution of ammonium chloride (10 ml) was added thereto, and the mixture was stirred at room temperature for 50 minutes. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride (200 ml) and extracted with ethyl acetate.

Workup

  1. stirringthe mixture was stirred at -78° C. for 2 hours
  2. stirringthe mixture was stirred at room temperature for 50 minutes
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-d0f91952a7cf435e8bb786f48a10034f
Source dataset
uspto-grants-1994_05
Patent number
US05308840

Reaction notes

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