Dimethylformamide → HCID 58259055, compound

HRID 509941Notes

Reaction equation

HRID 509941 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[N:6][CH:7]=1.C([Li])(C)(C)C.CN(C)[CH:24]=[O:25].[Cl-].[NH4+]>O1CCCC1>[F:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][NH:8][C:5]1[N:6]=[CH:7][C:2]([CH:24]=[O:25])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 29553240HCID 29553240, compoundHCID 178418306HCID 178418306, compound2×

Product 1

HCID 58259055HCID 58259055, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

In a round bottom flask, (5-bromo-pyridin-2-yl)-(2-fluoro-benzyl)-amine (40, 3.90 g, 13.9 mmol) was combined with 60.0 mL of tetrahydrofuran at −78° C. under nitrogen and tert-butyllithium (5.57 mL, 2.50 M in hexane) was added over 5 minutes. After 30 minutes additional tert-butyllithium (17.1 mL, 1.7 M in hexane) was added over 5 minutes. After 25 minutes, N,N-dimethylformamide (2.6 mL, 34 mmol) was added and the mixture was stirred for 70 minutes at −78° C., then allowed to warm up to room temperature for 1 hour. The reaction was poured into aqueous ammonium chloride and extracted with ethyl acetate. The organic portion was dried with sodium sulfate, filtered and filtrate concentrated under vacuum to provide the desired compound (41, 3.0 g), which was used in the next step without further purification.

Workup

  1. temperatureto warm up to room temperature for 1 hour
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic portion was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationfiltrate concentrated under vacuum

Sources & evidence

ORD record
ord-da3fd9e0717b44e49f5aff6c3dddf7ee
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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