Sodium borohydride → HCID 58514824, compound

HRID 449262Notes

Reaction equation

HRID 449262 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:11]3=[N:12][C:13]([C:16]4[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=4)=[CH:14][CH:15]=[C:10]3[N:9]=[N:8]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:11]3=[N:12][C:13]([C:16]4[CH:23]=[CH:22][C:19]([CH2:20][OH:21])=[CH:18][CH:17]=4)=[CH:14][CH:15]=[C:10]3[N:9]=[N:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 87228704HCID 87228704, compound

Product 1

HCID 58514824HCID 58514824, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of example 10 (0.095 g, 0.259 mmol) in methanol (2 ml) cooled to 0° C., sodium borohydride (0.010 g, 0.259 mmol) was added and stirred for 1 h. The reaction was quenched by the addition of ice-cold water, extracted with ethyl acetate, washed with brine, dried over sodium sulphate and concentrated. The crude product was purified by column chromatography with methanol:dichloromethane to afford the title compound as an off-white solid (0.040 g, 46%). M.P.: 210-213° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.61 (d, J=8.7 Hz, 1H), 8.22 (d, J=8.3 Hz, 2H), 8.11 (d, J=8.8 Hz, 1H), 7.53 (m, 4H), 7.21 (m, 2H), 5.98 (s, 2H), 5.32 (t, J=5.8 Hz, 1H), 4.59 (d, J=5.7 Hz, 2H). MS (m/z): 335.05 (M++1).

Workup

  1. customThe reaction was quenched by the addition of ice-cold water
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography with methanol

Sources & evidence

ORD record
ord-536872663fc945a09bf955e2d9c5bcb3
Source dataset
uspto-grants-2013_07
Patent number
US08481739B2

Reaction notes

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