Diisopropylethylamine → HCID 59152453, compound

HRID 423413Notes

Reaction equation

HRID 423413 reaction equation
[N:1]1([CH:6]2[CH:10]([OH:11])[CH2:9][NH:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:12][C:13]1[CH:14]=[CH:15][C:16](F)=[N:17][CH:18]=1.C(N(C(C)C)CC)(C)C>C(#N)C.C(=O)(O)[O-].[Na+]>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([N:8]2[CH2:9][C@@H:10]([OH:11])[C@H:6]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH2:7]2)=[N:17][CH:18]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27831685-Bromo-2-fluoropyridineHCID 50944249HCID 50944249, compound

Product 1

HCID 59152453HCID 59152453, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Dissolve [1,3′]bipyrrolidinyl-4′-ol (452 mg, 2.89 mmol) in acetonitrile (10 mL) and add 5-bromo-2-fluoro-pyridine (764 mg, 4.34 mmol) and diisopropylethylamine (1.26 mL, 7.23 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 (2N NH3)/CH2Cl2 to give 610 mg (67%) of the title compound as a yellow foam. MS/ES m/z (79Br) 312.0 [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 (2N NH3)/CH2Cl2

Sources & evidence

ORD record
ord-760a7fcf410b48029eb4c8f9e316e07a
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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