Boron tribromide → HCID 86625371, compound

HRID 1986242Notes

Reaction equation

HRID 1986242 reaction equation
C[O:2][C:3]1[C:8]2[S:9][C:10]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([NH:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]4)[N:13]=3)=[CH:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[CH3:28][N:25]1[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][CH2:19][NH:18][C:14]2[N:13]=[C:12]([C:10]3[S:9][C:8]4[C:3]([OH:2])=[CH:4][CH:5]=[CH:6][C:7]=4[CH:11]=3)[CH:17]=[CH:16][N:15]=2)[CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68854852HCID 68854852, compound

Product 1

HCID 86625371HCID 86625371, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

[4-(7-Methoxy-benzo[b]thiophen-2-yl)-pyrimidin-2-yl]-[3-(4-methyl-piperazin-1-yl)-propyl]-amine (150 mg, 0.380 mmol) is dissolved in dry dichloromethane (10 mL) and the solution is cooled to −70° C. To the solution, boron bromide (BBr3) (1.0 M in dichloromethane, 2.64 mL) is added dropwise. The reaction is stirred at −70° C. for 15 minutes, then the cool bath is removed and the reaction is allowed to warm to ambient temperature overnight. After 16 hours, the reaction is again cooled to 70° C. Methanol (5 mL) is added to the reaction mixture then the mixture is allowed to warm to ambient temperature where it is concentrated in vacuo to an orange solid. The crude product is dissolved in THF (minimal) and purified by silica gel chromatography, eluting with MeOH/dichloromethane 0-40%, to yield the title compound as a solid (92.0 mg, 63% yield). ES+(m/z) 384 [M+H].

Workup

  1. customthe cool bath is removed
  2. temperatureto warm to ambient temperature overnight
  3. waitAfter 16 hours
  4. temperaturethe reaction is again cooled to 70° C
  5. additionMethanol (5 mL) is added to the reaction mixture
  6. temperatureto warm to ambient temperature where it
  7. concentrationis concentrated in vacuo to an orange solid
  8. dissolutionThe crude product is dissolved in THF (minimal)
  9. custompurified by silica gel chromatography
  10. washeluting with MeOH/dichloromethane 0-40%

Sources & evidence

ORD record
ord-5fed413afd4a48c39aaff26a0eeaba3f
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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