Methanol → HCID 22038461, compound

HRID 1790031Notes

Reaction equation

HRID 1790031 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[CH2:15][CH2:14][NH:13][C:12](=O)[C:11]=2[C:10]([CH3:18])=[C:9]1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1.CO>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[CH2:15][CH2:14][NH:13][CH2:12][C:11]=2[C:10]([CH3:18])=[C:9]1[C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 22038494HCID 22038494, compound

Product 1

HCID 22038461HCID 22038461, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-chlorophenyl)-2-(4-chlorophenyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (2.84 g, 7.64 mmol, prepared as in Scheme 2 and in a similar manner to Example 22) in tetrahydrofuran (38 mL) was added borane-tetrahydrofuran complex (1 M, 76 mL) at 0° C. over 20 minutes. The mixture was heated at reflux for 3 h. The mixture was cooled to rt, methanol was added, and then the solvent was evaporated off. The residue was purified by silica gel chromatography. Elution first with ethyl acetate, followed by 10% methanol in methylene chloride, gave a colorless gum (950 mg, 34.8%). LC-MS m/z (MH+) 357.1, retention time 2.78 min (method 2).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. customthe solvent was evaporated off
  4. customThe residue was purified by silica gel chromatography
  5. washElution first with ethyl acetate

Sources & evidence

ORD record
ord-7fc9c81abdff47de8db2aee8312afd71
Source dataset
uspto-grants-2006_07
Patent number
US07071207B2

Reaction notes

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