Boron tribromide → 4-Chloro-3-[5-methyl-3-[4-(4-methyl-piperazine-1-sulfonyl)-phenylamino]-benzo[1,2,4]triazin-7-yl]-phenol

HRID 449209Notes

Reaction equation

HRID 449209 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[C:10]1[CH:36]=[C:35]([CH3:37])[C:13]2[N:14]=[C:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([N:28]4[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]4)(=[O:27])=[O:26])=[CH:21][CH:20]=3)[N:16]=[N:17][C:12]=2[CH:11]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:10]1[CH:36]=[C:35]([CH3:37])[C:13]2[N:14]=[C:15]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([S:25]([N:28]4[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]4)(=[O:26])=[O:27])=[CH:23][CH:24]=3)[N:16]=[N:17][C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59837790[7-(2-Chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[4-(4-methyl-piperazine-1-sulfonyl)-phenyl]-amine

Product 1

HCID 115337814-Chloro-3-[5-methyl-3-[4-(4-methyl-piperazine-1-sulfonyl)-phenylamino]-benzo[1,2,4]triazin-7-yl]-phenolYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[4-(4-methyl-piperazine-1-sulfonyl)-phenyl]-amine (1.0 equiv., 0.339 mmol) was dissolved in 10 mL anhydrous DCM, purged of air via house vacuum, then blanketed with argon. Neat BBr3 (4.0 equiv., 1.355 mmol) was added via syringe dropwise and allowed to stir at room temperature for 2 h. The reaction was quenched with saturated NaHCO3; the precipitate was filtered and rinsed with Et2O to afford crude orange solid. The compound was purified by prep. HPLC using 10-50-75 gradient, collecting peaks for 9-14 minutes. A yellow solid was recovered (70.5 mg, 40% yield). 1H NMR (DMSO-d6): δ 1.98 (s, 3H), 2.37 (bs, 4H), 2.72 (s, 3H), 2.90 (bs, 4H), 6.88 (dd, J=2.94 Hz, 8.81 Hz, 1H), 6.95 (d, J=2.92 Hz, 1H), 7.41 (d, J=8.79 Hz, 1H), 7.78 (d, J=8.89 Hz, 2H), 7.92 (m, 1H), 8.21 (d, J=1.35 Hz, 1H), 8.28 (d, J=8.88 Hz, 2H), 11.47 (s, 1H). MS (ES+): m/z=526 LC retention time: 2.30 minutes.

Workup

  1. custompurged of air via house vacuum
  2. customThe reaction was quenched with saturated NaHCO3
  3. filtrationthe precipitate was filtered
  4. washrinsed with Et2O
  5. customto afford crude orange solid
  6. customThe compound was purified by prep
  7. customcollecting peaks for 9-14 minutes
  8. customA yellow solid was recovered (70.5 mg, 40% yield)

Sources & evidence

ORD record
ord-4beab68dfb67490e9af9bdc88bc54092
Source dataset
uspto-grants-2013_07
Patent number
US08481536B2

Reaction notes

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