Sodium borohydride → HCID 59852849, compound

HRID 1670331Notes

Reaction equation

HRID 1670331 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-b2d938efed62498abb60d9c1f8b04e6b
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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