Dimethylformamide → HCID 59593345, compound

HRID 1024174Notes

Reaction equation

HRID 1024174 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, 2.00M in cyclohexane). After 90 minutes, tert-butyllithium (42.00 mL, 1.70M 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-fac16538ae414f42ba6babe4370f1a9a
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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