Chloroform → HCID 46186185, compound

HRID 341284Notes

Reaction equation

HRID 341284 reaction equation
[BH4-].[Na+].[C:3]1([S:9]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([CH:21]=[CH:22][N+:23]([O-:25])=[O:24])=[CH:18][CH:19]=3)[C:14]3[CH:26]=[C:27]([Cl:30])[CH:28]=[N:29][C:13]2=3)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(Cl)(Cl)Cl>C(O)(C)C>[C:3]1([S:9]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([CH2:21][CH2:22][N+:23]([O-:25])=[O:24])=[CH:18][CH:19]=3)[C:14]3[CH:26]=[C:27]([Cl:30])[CH:28]=[N:29][C:13]2=3)(=[O:10])=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 66765892HCID 66765892, compound

Product 1

HCID 46186185HCID 46186185, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

NaBH4 (46 mg, 2.5 equiv.) was added in small portions to a suspension of 14 (200 mg, 0.48 mmol) and 240 mg of silica (40-60 mesh) in a solution of chloroform and isopropanol (11.6 mL, 8.6:3). The solution was stirred for 1 h 30 at room temperature and then filtered through celite. Solvents were removed under reduced pressure and the crude product was purified by flash chromatography (CH2Cl2/PE 7:3) to afford 15 in 73% yield as a white solid, 1H-NMR (300 MHz, CDCl3): δ 8.49 (d, 1H, J=1.2 Hz), 8.41 (d, 1H, J=8.6 Hz), 8.14-8.10 (m, 3H), 7.74 (bs, 1H), 7.55 (t, 1H, J=7.5 Hz), 7.45-7.40 (m, 3H), 4.70 (t, 2H, J=7.1 Hz), 3.46 (t, 1H, J=7.1 Hz), 13C-NMR (75 MHz, CDCl3): δ 162.4 (C), 149.0 (C), 145.8 (CH), 138.4 (C), 137.7 (C), 134.3 (CH), 131.9 (C), 129.9 (CH), 129.2 (2 CH), 128.2 (CH), 127.7 (2C), 122.3 (C), 121.0 (CH), 119.4 (C), 115.7 (CH), 76.4 (CH2), 33.2 (CH2), MS (ESI) m/z 416 [M+H+]

Workup

  1. filtrationfiltered through celite
  2. customSolvents were removed under reduced pressure
  3. customthe crude product was purified by flash chromatography (CH2Cl2/PE 7:3)

Sources & evidence

ORD record
ord-c8f243f509884f01a1d56ba99c0eee39
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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