Boron tribromide → HCID 10371713, compound

HRID 374064Notes

Reaction equation

HRID 374064 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([S:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:29]([NH:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=3[F:39])=[O:30])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[C:11]([S:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:29]([NH:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=3[F:39])=[O:30])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10326923HCID 10326923, compound

Product 1

HCID 10371713HCID 10371713, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of N-[5-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-ylthio]pentyl]-N'-(2,4-difluorophenyl)-N-heptylurea (0.78 g, 0.0012 mol) in methylene chloride (30 mL) cooled to -78° under a nitrogen atmosphere, 1M boron tribromide in methylene chloride (3.6 mL) was added. The reaction mixture stirred for 1 hour at 0°, was poured over ice (100 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with 10% aqueous NaHCO3 (50 mL), water, brine, dried over magnesium sulfate, and concentrated in vacuo to give the crude oil. The product was purified by flash chromatography on silica gel (100 mL) eluting with hexane:ethyl acetate (40:60 v:v) to give a white foam, mp 110°-12° (0.5 g, 0.00008 mol). 1H NMR (DMSO-d6) δ12.22 (bs,1H), 9.55(bs,1H), 9.32(bs,1H),7.92(s,1H), 7.45-6.6(m,11H), 3.24(m,4H), 3.06(t,2H), 1.77-1.17(m,16H), 0.88(t,3H).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe combined organic layer was washed with 10% aqueous NaHCO3 (50 mL), water, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give the crude oil
  6. customThe product was purified by flash chromatography on silica gel (100 mL)
  7. washeluting with hexane:ethyl acetate (40:60 v:v)
  8. customto give a white foam, mp 110°-12° (0.5 g, 0.00008 mol)

Sources & evidence

ORD record
ord-fbbd09e13b37457c91ced3b2a8b242fd
Source dataset
uspto-grants-1992_11
Patent number
US05166214

Reaction notes

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