Sodium borohydride → HCID 59852849, compound

HRID 2374080Notes

Reaction equation

HRID 2374080 reaction equation
[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:6]=1[CH:19]=[O:20].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[C:6]=1[CH2:19][OH:20]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59852874HCID 59852874, compound

Product 1

HCID 59852849HCID 59852849, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To tert-butyl 4-(2-fluoro-4-nitrophenoxy)-3-formylpyridin-2-ylcarbamate (75 mg, 0.2 mmol) in methanol (1 mL) at 0° C. was added sodium borohydride (7.6 mg, 0.20 mmol). After stirring at 0° C. for 30 min, the reaction was quenched with saturated aqueous ammonium chloride solution (1 mL). The reaction was diluted with EtOAc (5 mL) and the layers were separated. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound (65 mg, 86%) as a white solid which was used without further purification. 1H NMR (CD3OD) δ 8.28 (dd, 1H, J=10.4, 2.8 Hz), 8.22-8.18 (m, 2H), 7.45 (t, 1H, J=8.4 Hz), 6.68 (d, 1H, J=6 Hz), 4.81 (s, 2H), 1.57 (s, 9H); MS(ESI+) m/z 380.27 (M+H)+.

Workup

  1. customthe reaction was quenched with saturated aqueous ammonium chloride solution (1 mL)
  2. additionThe reaction was diluted with EtOAc (5 mL)
  3. customthe layers were separated
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c0ba974fe1084d1fac2d8eab2b4a8a41
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

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