Dichloromethane → HCID 66834653, compound

HRID 61910Notes

Reaction equation

HRID 61910 reaction equation
C(Cl)Cl.C[O:5][C:6]1[CH:7]=[CH:8][C:9]2[C:21](=[O:22])[C:20]3[C:19]4[CH:18]=[CH:17][N:16]=[CH:15][C:14]=4[O:13][C:12]=3[C:11]([CH3:24])([CH3:23])[C:10]=2[CH:25]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>O>[OH:5][C:6]1[CH:7]=[CH:8][C:9]2[C:21](=[O:22])[C:20]3[C:19]4[CH:18]=[CH:17][N:16]=[CH:15][C:14]=4[O:13][C:12]=3[C:11]([CH3:23])([CH3:24])[C:10]=2[CH:25]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 668347578-Methoxy-10,10-dimethyl-10H-11-oxa-2-aza-benzo[b]fluoren-5-one

Product 1

HCID 66834653HCID 66834653, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

DCM (0.34 ml) solution of 8-methoxy-10,10-dimethyl-10H-11-oxa-2-aza-benzo[b]fluoren-5-one (Compound GT15-11, 10 mg) was cooled to −78° C., added with the DCM solution (0.17 ml) of 1.0 M BBr3, and the mixture was stirred at room temperature overnight. To the reaction mixture, water and saturated aqueous solution of sodium bicarbonate were added, and the solid produced therefrom was filtered off. The filtrate was extracted with the mixture solution of DCM and MeOH (DCM:MeOH=9:1). The organic layer was washed with saturated brine. The filtered solid and the residues obtained after concentration under reduced pressure were combined to obtain the title compound (9.5 mg, 99%).

Workup

  1. customthe solid produced
  2. filtrationtherefrom was filtered off
  3. extractionThe filtrate was extracted with the mixture solution of DCM and MeOH (DCM:MeOH=9:1)
  4. washThe organic layer was washed with saturated brine
  5. customThe filtered solid and the residues obtained
  6. concentrationafter concentration under reduced pressure

Sources & evidence

ORD record
ord-fefb7151f9f44f63afd02e00935a9022
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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