Boron tribromide → NSC248834

HRID 2175370Notes

Reaction equation

HRID 2175370 reaction equation
B(Br)(Br)Br.COC1C=CC(N2CC[N:16]([CH2:19][C:20]3[CH:21]=[C:22]4[NH:31][C:30](=[O:32])[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[N:23]4[CH:33]=3)CC2)=CC=1>C(Cl)Cl.CO>[O:32]=[C:30]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]2[CH:33]=[C:20]([C:19]#[N:16])[CH:21]=[C:22]2[NH:31]1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 71231650HCID 71231650, compound

Product 1

HCID 317322NSC248834Yield 22%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Under cooling on ice, boron tribromide (0.100 mL, 1.04 mmol) was added to a solution of 2-[4-(4-methoxyphenyl)piperazin-1-ylmethyl]pyrrolo[1,2-a]quinazolin-5(4H)-one (the above Compound 2-16, 200 mg, 0.515 mmol) in methylene chloride (3.0 mL). The reaction solution was stirred at room temperature for 1 hour. The reaction solution was diluted with methanol (2.0 mL) under cooling on ice, and then concentrated under reduced pressure. The obtained residue was dissolved in 1M sodium hydroxide aqueous solution (2.0 mL), and 2M hydrochloric acid was added so that pH of the solution was 7. The precipitate was collected by filtration, and dried under reduced pressure, to obtain title Compound 3-1 (43.2 mg, yield: 22%) as an orange powder.

Workup

  1. temperatureunder cooling on ice
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe obtained residue was dissolved in 1M sodium hydroxide aqueous solution (2.0 mL)
  4. addition2M hydrochloric acid was added so that pH of the solution
  5. filtrationThe precipitate was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-46ff7d56aeda4e59812fa2a0adde9842
Source dataset
uspto-grants-2015_06
Patent number
US09062061B2

Reaction notes

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