Methanol → HCID 178515671, compound

HRID 1013792Notes

Reaction equation

HRID 1013792 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([O:24]C)[CH:21]=[C:20]([Cl:26])[C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:18][CH2:17][C:16]3[C:12](=[CH:13][NH:14][N:15]=3)[CH2:11]2)[C:6]1=[O:19].B(Br)(Br)Br.CO>C(Cl)Cl>[Cl:26][C:20]1[CH:21]=[C:22]([OH:24])[CH:23]=[C:2]([Cl:1])[C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:18][CH2:17][C:16]3[C:12](=[CH:13][NH:14][N:15]=3)[CH2:11]2)[C:6]1=[O:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 178491896HCID 178491896, compound

Product 1

HCID 178515671HCID 178515671, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 3-(2,6-Dichloro-4-methoxy-benzyl)-1-(4,5,6,7-tetrahydro-2H-indazol-5-yl)-pyrrolidin-2-one (Example 1) (15.0 g, 38 mmol) in methylene chloride (1.5 L) and cool to 0° C. Treat with boron tribromide (19.9 mL, 190 mmol) dropwise over 30 minutes and allow reaction mixture to warm to room temperature. Stir for 28 h at room temperature, re-cool in an ice-bath, add methanol (38 mL) carefully over 15 minutes to the stirred reaction mixture. Remove organic solvents by rotary evaporator, and dissolve the residue in 4:1 chloroform/isopropyl alcohol (600 mL) and water (100 mL). Neutralize to pH 7 using 5 N NaOH, separate, reserve the organics and extract the aqueous layer with two portions of chloroform/isopropyl alcohol. Dry the combined organics over sodium sulfate, filter and evaporate to a solid and vacuum dry at 90° C. to yield 10.7 g (75%) of the titled compound. MS (m/z): 380 (m+1).

Workup

  1. customreaction mixture
  2. temperatureto warm to room temperature
  3. temperaturere-cool in an ice-bath
  4. customto the stirred reaction mixture
  5. customRemove organic solvents by rotary evaporator
  6. dissolutiondissolve the residue in 4:1 chloroform/isopropyl alcohol (600 mL) and water (100 mL)
  7. customseparate
  8. extractionreserve the organics and extract the aqueous layer with two portions of chloroform/isopropyl alcohol
  9. dry with materialDry the combined organics over sodium sulfate
  10. filtrationfilter
  11. customevaporate to a solid and vacuum
  12. customdry at 90° C.

Sources & evidence

ORD record
ord-6c43988f745b4d5d987679d8f6790762
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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