Dimethylformamide → HCID 59593345, compound

HRID 1952036Notes

Reaction equation

HRID 1952036 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[N:6][CH:7]=1.C([Li])CCC.C([Li])(C)(C)C.CN(C)[CH:29]=[O:30]>O1CCCC1.O>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:5]2[N:6]=[CH:7][C:2]([CH:29]=[O:30])=[CH:3][CH:4]=2)=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 975849HCID 975849, compoundHCID 178418306HCID 178418306, compoundHCID 178418339Butyllithium

Product 1

HCID 59593345HCID 59593345, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To (5-Bromo-pyridin-2-yl)-(4-chloro-benzyl)-amine (41, 10.00 g, 0.03360 mol) in tetrahydrofuran (400.0 mL) under an atmosphere of nitrogen at −78° C. was added n-butyllithium (17.5 mL, 2.00 M in cyclohexane). After 90 minutes, tert-butyllithium (42.00 mL, 1.70 M in hexane) was added to the reaction. After 80 minutes, N,N-dimethylformamide (6.9 mL, 0.089 mol) was added to the reaction. The reaction mixture was stirred at −78° C. for 2 hours, then allowed to warm to room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to give the crude compound, which was crystallized from tert-butoxyl methyl ether to provide compound (42, 7.66 g, 92.2%).

Workup

  1. waitAfter 80 minutes
  2. temperatureto warm to room temperature for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5158a3bb692b4c6d832da2de6702e58a
Source dataset
uspto-grants-2013_03
Patent number
US08404700B2

Reaction notes

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