Boron tribromide → HCID 11634592, compound

HRID 273516Notes

Reaction equation

HRID 273516 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:34]=[C:33]([CH3:35])[C:13]2[N:14]=[C:15]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([S:25][CH2:26][CH2:27][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)[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:34]=[C:33]([CH3:35])[C:13]2[N:14]=[C:15]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([S:25][CH2:26][CH2:27][N:28]4[CH2:29][CH2:30][CH2:31][CH2:32]4)[CH:20]=3)[N:16]=[N:17][C:12]=2[CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59837686HCID 59837686, compound

Product 1

HCID 11634592HCID 11634592, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-yl]-[3-(2-pyrrolidin-1-yl-ethylsulfanyl)-phenyl]-amine (1.0 equiv., 0.62 mmol) was dissolved in anhydrous DCM, purged of air using house vacuum, and placed under an argon blanket. Neat BBr3 (4.0 equiv., 2.5 mmol) was then added via syringe and allowed to stir at room temperature for 2 h. The reaction was quenched using saturated NaHCO3; the precipitate was filtered and washed with water and Et2O to afford a dark orange/brown solid. The compound was purified by flash chromatography using 90:10 DCM/MeOH to recover a burnt orange solid (64.6 mg, 22% yield). Rf=0.32 1H NMR (DMSO-d6): δ 1.68 (bs, 4H), 2.68 (s, 3H), 2.73 (bs, 2H), 3.14 (t, J=6.87 Hz, 2H), 6.87 (d, J=8.10 Hz, 1H), 6.93 (s, 1H), 7.03 (d, J=7.42 Hz, 1H), 7.34 (t, J=7.58 Hz, 1H), 7.40 (d, J=8.65 Hz, 1H), 7.77 (d, J=7.95 Hz, 1H), 8.16 (s, 2H), 9.93 (s, 1H), 11.01 (s, 1H). MS (ES+): m/z=493

Workup

  1. custompurged of air
  2. customThe reaction was quenched
  3. filtrationthe precipitate was filtered
  4. washwashed with water and Et2O
  5. customto afford a dark orange/brown solid
  6. customThe compound was purified by flash chromatography

Sources & evidence

ORD record
ord-9f21e9154789420f88114ca6051a9bc8
Source dataset
uspto-grants-2008_11
Patent number
US07456176B2

Reaction notes

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