Borane → 3-(Aminomethyl)-N-(3,5-dichlorobenzyl)-N-(4-fluorobenzyl)benzenesulfonamide

HRID 1889656Notes

Reaction equation

HRID 1889656 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:9]([N:12]([CH2:21][C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=2)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].B>C1COCC1>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([S:9]([N:12]([CH2:21][C:22]2[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=2)[CH2:13][C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 58531629HCID 58531629, compound

Product 1

HCID 585316133-(Aminomethyl)-N-(3,5-dichlorobenzyl)-N-(4-fluorobenzyl)benzenesulfonamideYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-cyano-N-(3,5-dichlorobenzyl)-N-(4-fluorobenzyl)benzenesulfonamide (0.9 g, 2.00 mmol) in THF (10 mL) at rt was added dropwise a solution of borane (1 M solution in THF) (16 mL, 16.02 mmol) under nitrogen atmosphere. The reaction mixture was stirred at rt. for 3 h, acidified by dropwise addition of TEA and it was stirred for 30 min. The solvents were removed and the residue was diluted with ethyl acetate and saturated aq NaHCO3 solution. The organic layer was separated, washed with brine, dried over MgSO4, and the crude product was purified by flash silica gel column chromatography on silica gel (ISCO. Column: 24 g. Eluent: A: CH2Cl2. B: 10% of 2 M ammonia in MeOH of ethyl acetate. Condition: A to 40% of B (45 min gradient) to obtain the desired product as a white solid (0.29 g, 32%). 1H NMR (CDCl3): δ 7.82 (s, 1H), 7.75 (d, J=8.0 Hz, 1H), 7.63 (d, J=8.0 Hz, 1H), 7.54 (t, J=8.0 Hz, 1H), 7.20-7.19 (m, 1H), 7.11-7.08 (m, 2H), 6.97-6.92 (m, 2H), 6.86-6.85 (m, 2H), 4.32 (s, 2H), 4.26 (s, 2H), 4.00 (s, 2H), 1.58 (bs, 2H); MS (ESI): [M+H]+=452.9.

Workup

  1. additionacidified by dropwise addition of TEA and it
  2. stirringwas stirred for 30 min
  3. customThe solvents were removed
  4. additionthe residue was diluted with ethyl acetate and saturated aq NaHCO3 solution
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. customthe crude product was purified by flash silica gel column chromatography on silica gel (ISCO

Sources & evidence

ORD record
ord-fbab81be619b4f79826b9e4847c1c6c5
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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