Sodium hydride → HCID 68536722, compound

HRID 1931443Notes

Reaction equation

HRID 1931443 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.FC1C=C(C2N=CC(CCC(N3CCCCC3)=O)=CC=2)C=CC=1.[H-].[Na+].[C:47]([O:51][C:52](=[O:55])[CH2:53]Br)([CH3:50])([CH3:49])[CH3:48]>CN(C=O)C>[C:47]([O:51][C:52](=[O:55])[CH2:53][NH:14][C:11]1[CH:12]=[N:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:9][CH:10]=1)([CH3:50])([CH3:49])[CH3:48]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 46311896HCID 46311896, compoundHCID 68536650HCID 68536650, compound

Product 1

HCID 68536722HCID 68536722, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon, 300 mg (1.59 mmol) of 6-(4-fluoro-phenyl)-pyridin-3-ylamine (prepared analogously as described in Example 76(a) and (b)) and 104 mg (2.39 mmol) of sodium hydride (55% in mineral oil) in DMF were stirred at room temperature for 30 min. Then 466.4 mg (2.39 mmol) of bromoacetic acid tert-butyl ester were added and the reaction mixture was stirred for 2 h at room temperature and for 5 h at 100° C. After evaporation, water and ethyl acetate were added. The organic phase was separated, dried and evaporated. Yield: 480 mg.

Workup

  1. stirringthe reaction mixture was stirred for 2 h at room temperature and for 5 h at 100° C
  2. customAfter evaporation, water and ethyl acetate
  3. additionwere added
  4. customThe organic phase was separated
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-16e9875ee4e84847a98f8f3d4c6ce1e2
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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