Diboron → HCID 10670600, compound

HRID 2287387Notes

Reaction equation

HRID 2287387 reaction equation
B#B.[C:3]([NH:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[C:12]2[S:17]([NH:20][C:21]1[C:26]([O:27][CH3:28])=[N:25][C:24]([Br:29])=[CH:23][N:22]=1)(=[O:19])=[O:18])(=O)[CH3:4]>C1COCC1>[CH2:3]([NH:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[C:12]2[S:17]([NH:20][C:21]1[C:26]([O:27][CH3:28])=[N:25][C:24]([Br:29])=[CH:23][N:22]=1)(=[O:19])=[O:18])[CH3:4]

Participants

4

Reactant 2

HCID 6328200DiboronHCID 10789754HCID 10789754, compound

Product 1

HCID 10670600HCID 10670600, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.0M solution of diborane in THF (6.65 ml) was added to a solution of 5-acetamido-N-(5-bromo-3-methoxy-2-pyrazinyl)-1-naphthalenesulphonamide (0.725 g) in dry THF (60 ml) at 0° C. under argon. The solution was heated under reflux for 24 hours and then volatile material was removed by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (7:13 v/v), to give 5-ethylamino-N-(5-bromo-3-methoxy-2-pyrazinyl)-1-naphthalenesulphonamide (0.23 g), m.p. 216-218° C. (after trituration with ether); 1H NMR (d6 -DMSO): 1.3 (t,3H), 3.25 (q,2H), 3.9 (s,3H), 6.6 (d,1H), 7.4-7.6 (m,2H), 7.75 (s,1H), 7.95 (d,1H), 8.25 (d,1H), 8.5 (d,1H), 11.3-11.5 (br, 1H); mass spectrum (+ve FAB, methanol/NBA): 438 (M+H)+.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 24 hours
  3. customvolatile material was removed by evaporation
  4. customThe residue was purified by flash chromatography
  5. washeluting with ethyl acetate/hexane (7:13 v/v)

Sources & evidence

ORD record
ord-05ecacff02af40edb6a21851c6cae225
Source dataset
uspto-grants-2000_07
Patent number
US06083951

Reaction notes

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