Sodium hydride → HCID 57527174, compound

HRID 1671817Notes

Reaction equation

HRID 1671817 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:13]([C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[O:17])[C:14]#[N:15])=[N:6][C:7]=1[S:8]([CH2:11]C)(=O)=O.[H-].[Na+]>CN(C=O)C>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:16](=[O:17])[CH:13]([C:5]1[N:6]=[C:7]2[S:8][C:11]([NH:1][CH:2]([CH3:3])[CH3:7])=[N:1][C:2]2=[CH:3][CH:4]=1)[C:14]#[N:15]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 67343379HCID 67343379, compound

Product 1

HCID 57527174HCID 57527174, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(5-amino-6-(ethylsulfonyl)pyridin-2-yl)-3-(2-fluorophenyl)-3-oxopropanenitrile (presumed 0.951 mmol, 1.0 eq.) and iPrNCS (0.15 mL, 1.43 mmol, 1.5 eq.) in DMF (4.8 mL) under nitrogen at 0° C. was added NaH (95%; 0.0982 g, 3.89 mmol, 4.1 eq.). After 0.75 hr, the cold bath was removed and the reaction was stirred to room temperature for 0.5 hr. At 0° C., iPrNCS (0.1 mL) and NaH (0.050 g) were added and stirred for 0.25 hr. The cold bath was removed, and the reaction was stirred to room temperature overnight. At 0° C., water and EtOAc were added, and separated. The aqueous layer was washed with EtOAc (2×). The aqueous layer was concentrated in vacuo. Silica gel chromatrography using CH2Cl2:MeOH (100:1) as eluent afforded 3-(2-fluorophenyl)-2-(2-(isopropylamino)thiazolo[5,4-b]pyridin-5-yl)-3-oxopropanenitrile as a burgundy solid (0.10 g, 29%).

Workup

  1. customthe cold bath was removed
  2. additionAt 0° C., iPrNCS (0.1 mL) and NaH (0.050 g) were added
  3. stirringstirred for 0.25 hr
  4. customThe cold bath was removed
  5. stirringthe reaction was stirred to room temperature overnight
  6. additionAt 0° C., water and EtOAc were added
  7. customseparated
  8. washThe aqueous layer was washed with EtOAc (2×)
  9. concentrationThe aqueous layer was concentrated in vacuo

Sources & evidence

ORD record
ord-977ae7578acc4eb8a9e58837d1c151c1
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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