Boron tribromide → HCID 72190206, compound

HRID 523880Notes

Reaction equation

HRID 523880 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:11]([C:17]3[C:21]([Cl:22])=[C:20]([Cl:23])[NH:19][C:18]=3[C:24](=[O:33])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31]C)[C:12]([Cl:16])=[C:13]([Cl:15])[CH:14]=2)=[O:9])=[C:4]([O:34]C)[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:11]([C:17]3[C:21]([Cl:22])=[C:20]([Cl:23])[NH:19][C:18]=3[C:24](=[O:33])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[OH:31])[C:12]([Cl:16])=[C:13]([Cl:15])[CH:14]=2)=[O:9])=[C:4]([OH:34])[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 117958214HCID 117958214, compound

Product 1

HCID 72190206HCID 72190206, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Compound 5 (33 mg, 0.058 mmol) in anhydrous DCM (1 mL) was slowly added 1.0 M solution of BBr3 in DCM (23 μL, 0.23 mmol, 4 eq.) via a syringe under N2 at −78° C. After being stirred for 0.5 h, the mixture was quenched by addition of MeOH (0.5 mL) and extracted with DCM (3×10 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated in vacuum. The residue was purified by column chromatography (silica gel, hexanes: 12% EtOAc) to give Compound 2 (30 mg, 96% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 11.34 (s, 1H), 10.39 (s, 1H), 9.77 (s, 1H), 7.47 (d, J=8.6 Hz, 1H), 7.43 (dd, J=8.0, 1.7 Hz, 1H), 7.36 (ddd, J=8.8, 7.4, 1.6 Hz, 1H), 7.04 (d, J=2.0 Hz, 1H), 6.95-6.90 (m, 1H), 6.87 (dd, J=8.6, 2.0 Hz, 1H), 6.68 (s, 1H), 6.53 (ddd, J=8.0, 7.3, 1.1 Hz, 1H); HRMS (ESI-TOF) [M+H]+ calcd for C22H12Cl5N2O4 542.9234. found 542.9237; HPLC purity 96.6%.

Workup

  1. customat −78° C
  2. customthe mixture was quenched by addition of MeOH (0.5 mL)
  3. extractionextracted with DCM (3×10 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe residue was purified by column chromatography (silica gel, hexanes: 12% EtOAc)

Sources & evidence

ORD record
ord-095b3f420b6e494bab355b2036616826
Source dataset
uspto-grants-2016_05
Patent number
US09340501B2

Reaction notes

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