Diisopropylethylamine → HCID 86638158, compound

HRID 423415Notes

Reaction equation

HRID 423415 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:7][NH:6][CH2:5][CH:4]1[OH:8].[Br:9][C:10]1[CH:11]=[CH:12][C:13](F)=[N:14][CH:15]=1.C(N(C(C)C)CC)(C)C>C(#N)C.C(=O)(O)[O-].[Na+]>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([N:6]2[CH2:7][C@@H:3]([NH:2][CH3:1])[C@H:4]([OH:8])[CH2:5]2)=[N:14][CH:15]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27831685-Bromo-2-fluoropyridineHCID 19691470HCID 19691470, compound

Product 1

HCID 86638158HCID 86638158, compoundYield 39.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Dissolve 4-methylamino-pyrrolidin-3-ol (430 mg, 3.29 mmol) in acetonitrile (10 mL) and add 5-bromo-2-fluoro-pyridine (868 mg, 4.93 mmol) and diisopropylethylamine (0.688 mL, 3.95 mmol). Reflux the mixture for 3 days. Dilute the mixture with saturated sodium bicarbonate and extract with dichloromethane (3×). Combine the organic fractions, dry over sodium sulfate, filter, and evaporate. Purify by silica gel chromatography, eluting with 0-7.5% methanol in dichloromethane with 2N ammonia to give 352 mg (37%) of the title compound as a yellow foam. MS/ES m/z (79Br) 272.0 [M+H]+.

Workup

  1. temperatureReflux the mixture for 3 days
  2. extractionextract with dichloromethane (3×)
  3. dry with materialCombine the organic fractions, dry over sodium sulfate
  4. filtrationfilter
  5. customevaporate
  6. customPurify by silica gel chromatography
  7. washeluting with 0-7.5% methanol in dichloromethane with 2N ammonia

Sources & evidence

ORD record
ord-e608b5913b7f4bfd9b7a52c3efd8fb16
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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