Water → HCID 23503283, compound

HRID 1835173Notes

Reaction equation

HRID 1835173 reaction equation
[CH:1]1([CH2:4][C:5]2[C:10]3[S:11][C:12]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=4)=[C:13]([O:14]C)[C:9]=3[C:8](=[O:27])[N:7]([CH3:28])[N:6]=2)[CH2:3][CH2:2]1.B(Br)(Br)Br.O>ClCCl>[CH:1]1([CH2:4][C:5]2[C:10]3[S:11][C:12]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=4)=[C:13]([OH:14])[C:9]=3[C:8](=[O:27])[N:7]([CH3:28])[N:6]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 23503254HCID 23503254, compound

Product 1

HCID 23503283HCID 23503283, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-15 °C

Procedure

7-Cyclopropylmethyl-3-methoxy-5-methyl-2-[(3-trifluoromethylphenyl)methyl]-thieno[2,3-d]pyridazin-4(5H)-one (8.8 g) was dissolved in dichloromethane (250 ml) and cooled to −15° C. Boron tribromide in dichloromethane (1M, 24 ml) was added. The reaction was allowed to warm to room temperature and left to stir for 72 hours. Water was added and the mixture was extracted with ethyl acetate. The ethyl acetate was dried, filtered and concentrated. The residue was purified by chromatography, eluting with 1:1 isohexane:ether, and then recrystallised from isohexane to give the sub-title compound (4.5 g).

Workup

  1. temperatureto warm to room temperature
  2. waitleft
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe ethyl acetate was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography
  8. washeluting with 1:1 isohexane
  9. customether, and then recrystallised from isohexane

Sources & evidence

ORD record
ord-a7bcd73aa90f4312b663e1fdce419a44
Source dataset
uspto-grants-2004_08
Patent number
US06770646B2

Reaction notes

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