Diboron → HCID 10670600, compound

HRID 343374Notes

Reaction equation

HRID 343374 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-ea88787a4a4c4cfdbcf11d159c88556c
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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