Water → {1-[4-(7-Amino-6-bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

HRID 1037275Notes

Reaction equation

HRID 1037275 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23](=[O:24])[C:22]4[CH:25]=[CH:26][C:27]([NH2:29])=[CH:28][C:21]=4[O:20][C:19]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Br:37]N1C(=O)CCC1=O.O>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:23](=[O:24])[C:22]4[C:21](=[CH:28][C:27]([NH2:29])=[C:26]([Br:37])[CH:25]=4)[O:20][C:19]=3[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 67067858{1-[4-(7-Amino-4-oxo-2-phenyl-4H-1-benzopyran-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 67067953{1-[4-(7-Amino-6-bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterYield 61%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of {1-[4-(7-amino-4-oxo-2-phenyl-4H-1-benzopyran-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (48 mg, 0.10 mmol) in chloroform (1.0 mL), was added N-bromosuccinimide (18 mg, 0.10 mmol) and the reaction mixture was stirred at RT for 1 hour. After this time, the mixture was poured into water and extracted with EtOAc (×2). The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2, gradient 0 to 80% EtOAc in pentane) to yield the title compound as a yellow solid (34 mg, 61%). LCMS (Method B): RT=4.96 min, [M+H]+=561/563.

Workup

  1. extractionextracted with EtOAc (×2)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash chromatography (SiO2, gradient 0 to 80% EtOAc in pentane)

Sources & evidence

ORD record
ord-93330130d221434f8c42cf9e9071ff93
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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