3-Bromopyridine → HCID 18518611, compound

HRID 1369111Notes

Reaction equation

HRID 1369111 reaction equation
[Li]CCCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[CH2:13]([N:15]([CH2:30][CH3:31])[CH2:16][CH2:17][N:18]1[C:28]2[C:23](=[C:24]([Br:29])[CH:25]=[CH:26][CH:27]=2)[C:21](=[O:22])[C:19]1=[O:20])[CH3:14].N1C2C(=CC=CC=2)C(=O)C1=O.[NH4+].[Cl-]>CCOCC>[CH2:30]([N:15]([CH2:13][CH3:14])[CH2:16][CH2:17][N:18]1[C:28]2[C:23](=[C:24]([Br:29])[CH:25]=[CH:26][CH:27]=2)[C:21]([OH:22])([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[C:19]1=[O:20])[CH3:31]

Participants

6

Reactant 4

HCID 122863-BromopyridineHCID 25517Ammonium ChlorideHCID 18518583HCID 18518583, compoundHCID 178418339Butyllithium

Product 1

HCID 18518611HCID 18518611, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of n-BuLi (0.16 mL, 1.0 eq, 1.53 M in hexanes) at −78° C., in anhydrous Et2O (1.0 mL), and under a nitrogen atmosphere was added a solution of 3-bromopyridine (40.8 mg, 0.0249 mL, 1.05 eq) in anhydrous Et2O (0.5 mL). The resulting light yellow coloured precipitate was stirred at −78° C. for 30 minutes and then a solution of isatin 1-(2-diethylaminoethyl)-4-bromoisatin (80.0 mg, 2.46×10−4), in anhydrous Et2O (1.5 mL) was added dropwise. The solution was stirred for a further 7.5 hours. Saturated aqueous NH4Cl (1.5 mL) was added to the resulting brown coloured reaction mixture and the reaction was allowed to warm to room temperature. The mixture was extracted with EtOAc and the combined extracts were dried (anhydrous Na2SO4). After filtration, the solvent was removed in vacuo. Purification was carried out by column chromatography (silica gel, 1% to 1.5% to 2% MeOH in CHCl3) to yield the title compound as a light yellow oil (35.5 mg, 36%).

Workup

  1. stirringThe solution was stirred for a further 7.5 hours
  2. temperatureto warm to room temperature
  3. extractionThe mixture was extracted with EtOAc
  4. dry with materialthe combined extracts were dried (anhydrous Na2SO4)
  5. filtrationAfter filtration
  6. customthe solvent was removed in vacuo
  7. customPurification

Sources & evidence

ORD record
ord-91d1af382f05490cb3e046e016df40cc
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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