2-Bromopyridine → HCID 66750139, compound

HRID 1749158Notes

Reaction equation

HRID 1749158 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.CON(C)[C:11](=[O:23])[CH2:12][C:13]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:16][CH2:15][CH2:14]1>O1CCCC1.CCOCC.[NH4+].[Cl-]>[C:17]1([C:13]2([CH2:12][C:11]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=3)=[O:23])[CH2:16][CH2:15][CH2:14]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 2

HCID 79732-BromopyridineHCID 87134254HCID 87134254, compound

Product 1

HCID 66750139HCID 66750139, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-bromopyridine (1.0 g, 4.3 mmol) in dry tetrahydrofuran (30 mL) 1.6 M n-butyl lithium in hexanes (4.8 mL) was added dropwise at −78° C. The mixture was kept at this temperature for 1 hour, followed by addition of a solution of Example 68D in tetrahydrofuran. At the end of addition, the mixture was allowed to reach ambient temperature and stirred at 60° C. for 2 hours. The mixture was then cooled to 0° C., and diluted with ether (50 mL) and saturated aqueous NH4Cl (60 mL). The organic phase was separated, dried over Na2SO4, filtered, and concentrated. The crude product was used in the next step without further purification (1.5 g, 5.97 mmol).

Workup

  1. additionAt the end of addition
  2. customto reach ambient temperature
  3. temperatureThe mixture was then cooled to 0° C.
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was used in the next step without further purification (1.5 g, 5.97 mmol)

Sources & evidence

ORD record
ord-5eab326a88f94d61afa8f8b5014eed89
Source dataset
uspto-grants-2015_10
Patent number
US09156788B2

Reaction notes

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