1,2-Dichloroethane → HCID 68086557, compound

HRID 1405066Notes

Reaction equation

HRID 1405066 reaction equation
[Br:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:6]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 8179723-Bromoisonicotinic acid

Product 1

HCID 68086557HCID 68086557, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-bromoisonicotinic acid (0.250 g, 1.238 mmol) in DMF (1.5 mL) was added pyrrolidine (0.097 g, 1.361 mmol), EDC (0.285 g, 1.485 mmol), and HOBt (0.227 g, 1.485 mmol) resulting in a homogenous solution. After stirring at room temperature 3 hours, the reaction mixture was dissolved in a saturated aqueous solution of sodium bicarbonate (20 mL) and extracted with EtOAc (2×20 mL). The combined organics were washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to provide Intermediate 12A as a colorless oil (0.219 g, 0.850 mmol, 68.7% yield). HPLC Ret timea: 1.463 min. MS (ES): m/z=257.0 [M+H]+. 1H NMR (400 MHz, acetone) δ ppm 1.77-2.03 (m, 4 H) 3.20 (t, J=6.40 Hz, 2 H) 3.55 (t, J=6.65 Hz, 2 H) 7.38 (d, J=4.27 Hz, 1 H) 8.63 (d, J=4.77 Hz, 1 H) 8.78 (s, 1 H).

Workup

  1. customresulting in a homogenous solution
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7a55547fccd4bb9ac48843a8ac5369e
Source dataset
uspto-grants-2014_12
Patent number
US08916553B2

Reaction notes

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