Water → HCID 178519045, compound

HRID 1046804Notes

Reaction equation

HRID 1046804 reaction equation
[F:1][C:2]1[C:26](/[N:27]=[CH:28]\[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][C:5]1[C:6](=[O:22])[O:7][C:8]2[CH:15]=[C:14]([O:16][C:17]3[S:18][CH:19]=[CH:20][N:21]=3)[CH:13]=[CH:12][C:9]=2[C:10]=1[CH3:11].[Br:35]N1C(=O)CCC1=O.O>C1COCC1>[Br:35][CH2:11][C:10]1[C:9]2[CH:12]=[CH:13][C:14]([O:16][C:17]3[S:18][CH:19]=[CH:20][N:21]=3)=[CH:15][C:8]=2[O:7][C:6](=[O:22])[C:5]=1[CH2:4][C:3]1[CH:23]=[CH:24][CH:25]=[C:26](/[N:27]=[CH:28]\[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:2]=1[F:1]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 178422688HCID 178422688, compound

Product 1

HCID 178519045HCID 178519045, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

THF (4.5 mL) was added to 3-(2-fluoro-3-{[1-phenyl-meth-(Z)-ylidene]-amino}-benzyl)-4-methyl-7-(thiazol-2-yloxy)-2-oxo-2H-1-benzopyran (compound 6a-3-4-1P) (226 mg), and the mixed solution was stirred at −78° C. for 20 minutes, and further stirred at 0° C. for 1 hour to yield a dark brown solution. This solution was added over 10 minutes to a solution of N-bromosuccinimide (178 mg) in THF (3.0 mL) (which had been prepared in advance in a separate container), and the mixture was further stirred at 0° C. for 1 hour. The reaction solution was added to water (5 mL) to complete the reaction, and the solution was extracted with ethyl acetate. The resultant organic layer extraction liquid was washed with saturated saline, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was then distilled away under reduced pressure, and a residue (320 mg) containing the title compound was obtained.

Workup

  1. stirringfurther stirred at 0° C. for 1 hour
  2. customto yield a dark brown solution
  3. customhad been prepared in advance in a separate container), and the mixture
  4. stirringwas further stirred at 0° C. for 1 hour
  5. customthe reaction
  6. extractionthe solution was extracted with ethyl acetate
  7. extractionThe resultant organic layer extraction liquid
  8. washwas washed with saturated saline
  9. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  10. distillationThe solvent was then distilled away under reduced pressure
  11. additiona residue (320 mg) containing the title compound
  12. customwas obtained

Sources & evidence

ORD record
ord-9e07ad7a331e474f8c7883fe7a7f75f5
Source dataset
uspto-grants-2013_10
Patent number
US08569378B2

Reaction notes

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