Boron tribromide → HCID 10248135, compound

HRID 2373498Notes

Reaction equation

HRID 2373498 reaction equation
B(Br)(Br)Br.[C:5]([C:9]1[CH:32]=[CH:31][C:12]([CH2:13][N:14]2[C:22]3[C:17](=[CH:18][C:19]([O:23]C)=[CH:20][CH:21]=3)[C:16]3[C:25](=[O:30])[C:26](=[O:29])[O:27][CH2:28][C:15]2=3)=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6]>C(Cl)Cl>[C:5]([C:9]1[CH:32]=[CH:31][C:12]([CH2:13][N:14]2[C:22]3[C:17](=[CH:18][C:19]([OH:23])=[CH:20][CH:21]=3)[C:16]3[C:25](=[O:30])[C:26](=[O:29])[O:27][CH2:28][C:15]2=3)=[CH:11][CH:10]=1)([CH3:8])([CH3:6])[CH3:7]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21964307HCID 21964307, compound

Product 1

HCID 10248135HCID 10248135, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (2.2 mL, 23.3 mmol) was added dropwise to a stirring suspension of 9-(4-tert-Butylbenzyl)-6-methoxy-1,9-dihydropyrano[3,4-b]indole-3,4-dione(4.92 g, 13.0 mmol) in methylene chloride (25 mL) at −78° C. under a nitrogen atmosphere over a period of 20 minutes. The mixture was then warmed up to room temperature. After stirring at room temperature for 6.5 hours, the reaction mixture was carefully quenched with a small amount of water and the evaporated to dryness. The residue was stirred in ether and filtered to afford a brown solid. Crystallization from aqueous methanol afforded the title compound as a brown solid (1.72 g). Mass spectrum (ESI, [M−H]−) m/z 362. 1HNMR (400 MHz, DMSO-d6): δ 9.39 (s, 1H), 7.44 (d, 1H, J=8.85 Hz), 7.40 (d, 1H, J=2.29 Hz), 7.34 (d, 2H, J=8.25 Hz), 6.80 (dd, 1H, J=8.86 and 2.29 Hz), 5.84 (s, 2H), 5.37 (s, 2H), 1.22 ppm (s, 9H).

Workup

  1. customthe reaction mixture was carefully quenched with a small amount of water
  2. customthe evaporated to dryness
  3. stirringThe residue was stirred in ether
  4. filtrationfiltered
  5. customto afford a brown solid
  6. customCrystallization from aqueous methanol

Sources & evidence

ORD record
ord-25a7cf7d7c9b4d9f9a21f7fbe3b74630
Source dataset
uspto-grants-2008_12
Patent number
US07459478B2

Reaction notes

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