Water → HCID 11574511, compound

HRID 229387Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[CH:13][CH:14]=[C:7]1[CH:6]([CH3:15])[N:5]2[C:16](=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[CH:18]=1.B(Cl)(Cl)Cl.O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[CH:13][CH:14]=[C:7]1[CH:6]([CH3:15])[N:5]2[C:16]([C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1)=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 7-bromo-5-(3-methoxybenzoyl)-4-methyl-4,5-dihydropyrrolo[1,2-a]quinoxaline (240 mg, 0.60 mmol) and tetrabutylammonium iodide (558 mg, 1.51 mmol) in methylene chloride (5 mL) at −78° C., under nitrogen, was treated with a 1 M solution of boron trichloride in methylene chloride (1.51 mL, 1.51 mmol). The reaction was then warmed to 0° C. and was stirred for 4 h. Ice and water was added to the reaction which was stirred to 30 min. The reaction was then diluted with a saturated aqueous solution of sodium bicarbonate, and the product was extracted with methylene chloride (3×25 mL). The product was purified via Biotage Horizon® (25S, silica, gradient from 15% EtOAc/hexane to 60% EtOAc/hexane) to yield 196 mg (85%) of 3-[(7-bromo-4-methylpyrrolo[1,2-a]quinoxalin-5(4H)-yl)carbonyl]phenol as a white foam. MS (ESI) m/z 383/385 ([M+H]+); MS (ESI) m/z 381/383 ([M−H]−); HRMS: calcd for C19H15BrN2O2, 382.0317; found (ESI+), 383.03805.

Workup

stirringwas stirred to 30 min
extractionthe product was extracted with methylene chloride (3×25 mL)
customThe product was purified via Biotage Horizon® (25S, silica, gradient from 15% EtOAc/hexane to 60% EtOAc/hexane)

Sources & evidence

ORD record: ord-16252f287d5c425c89fb1797818e19d3
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07563793B2

Reaction notes

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