Water → HCID 22220927, compound

HRID 1794273Notes

Reaction equation

HRID 1794273 reaction equation
C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][N:8]3[C:14]([C:15]4[C:16]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)=[N:17][O:18][C:19]=4[CH3:20])=[N:13][N:12]=[C:9]32)=[CH:5][CH:4]=1.[B].C(OCC)C.O>ClCCl>[CH3:20][C:19]1[O:18][N:17]=[C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]=1[C:14]1[N:8]2[CH2:7][C:6]3[C:10]([C:9]2=[N:12][N:13]=1)=[CH:11][C:3]([OH:2])=[CH:4][CH:5]=3

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 5462311BoronHCID 10337549HCID 10337549, compound

Product 1

HCID 22220927HCID 22220927, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

8-Methoxy-3-(5-methyl-3-phenylisoxazol-4-yl)-5H-[1,2,4]triazolo[3,4-a]isoindole (4.6 g, 13 mmol) in dichloromethane (70 ml) was stirred with boron tribronide (25 g) for five days. The reaction was cooled to −78° C. and diethyl ether was added dropwise followed by water. The reaction was warmed to room temperature and the organic layer was washed with water and dried, filtered and evaporated. The residue was purified by column chromatography on silica using methanol/dichloromethane to yield the title compound.

Workup

  1. temperatureThe reaction was warmed to room temperature
  2. washthe organic layer was washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-5278e45ab9854574a7758498de783ae9
Source dataset
uspto-grants-2006_04
Patent number
US07022724B2

Reaction notes

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