Acetic Acid → HCID 131724211, compound

HRID 460167Notes

Reaction equation

HRID 460167 reaction equation
[Br:1][C:2]1[N:7]=[C:6](C=O)[CH:5]=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[BH-](OC(C)=O)(OC(C)=O)O[C:18](C)=O.[Na+].CC(O)=O>ClC(Cl)C>[Br:1][C:2]1[C:3]([CH3:18])=[CH:4][CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[N:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 27570096-Bromopyridine-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 131724211HCID 131724211, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of 6-bromo-2-pyridine-carboxaldehyde (200 mg, 1.08 mmol) in dichloroethane (10 mL) was added morpholine (0.14 mL, 1.62 mmol) followed by NaBH(OAc)3 (458 mg, 2.16 mmol) and AcOH (0.25 mL, 4.32 mmol). The resulting mixture was stirred at RT for 12 h. The reaction was quenched with 2M Na2CO3 solution and stirred 1 h. The mixture was poured into Et2O and washed with 2 M Na2CO3 solution. The organic layer was collected, dried over Na2SO4 and concentrated in vacuo to give 2-bromo-6-morpholinyl-methylpyridine as a white solid. MS m/z: 256.9 (M+H).

Workup

  1. customThe reaction was quenched with 2M Na2CO3 solution
  2. stirringstirred 1 h
  3. additionThe mixture was poured into Et2O
  4. washwashed with 2 M Na2CO3 solution
  5. customThe organic layer was collected
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-904f26b272a54995a9b8df17beeedc49
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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