2-Bromopyridine → HCID 67103776, compound

HRID 45446Notes

Reaction equation

HRID 45446 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[CH2:13]([O:20][C:21]1[C:26]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:25][CH:24]=[CH:23][C:22]=1[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]=[O:38])[CH:32]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:13]([O:20][C:21]1[C:26]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:25][CH:24]=[CH:23][C:22]=1[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[OH:38])[CH:32]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 79732-BromopyridineHCID 25517Ammonium ChlorideHCID 866528592'-(Benzyloxy)-3'-tert-butylbiphenyl-3-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 67103776HCID 67103776, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-bromopyridine (1.51 g, 9.58 mmol) in dry tetrahydrofuran (20 mL) was stirred under nitrogen at −78° C. and 2.5M n-butyllithium in hexanes (3.8 mL, 9.5 mmol) was added at such a rate that the temperature did not exceed −70° C. Stirring was continued at −78° C. for 30 min. when a solution of 9 (2.1 g, 6.1 mmol) in tetrahydrofuran (15 mL) was added at such a rate that the temperature did not exceed −65° C. Stirring was continued at −78° C. for 20 min., then for 2 hr at room temperature. The reaction mixture was poured on saturated ammonium chloride (150 mL) and extracted with ethyl acetate (200 mL). The organic extract was washed with water (2×100 mL), dried over sodium sulfate and stripped. The crude 10 was used as such in the next step.

Workup

  1. customdid not exceed −70° C
  2. customdid not exceed −65° C
  3. stirringStirring
  4. waitwas continued at −78° C. for 20 min.
  5. waitfor 2 hr at room temperature
  6. extractionextracted with ethyl acetate (200 mL)
  7. extractionThe organic extract
  8. washwas washed with water (2×100 mL)
  9. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-16b60a99f77e4feba96d1977ee48f459
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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