Acetic Acid → HCID 18771613, compound

HRID 460200Notes

Reaction equation

HRID 460200 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=O)[CH3:9])[CH:5]=[CH:4][CH:3]=1.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH3:9])[N:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 112985782-Acetyl-6-bromopyridine

Product 1

HCID 18771613HCID 18771613, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 1-(6-bromo-pyridin-2-yl)-ethanone (600 mg, 3.01 mmol) in dry CH2Cl2 (20 mL) was added piperidine (0.5 mL) followed by NaBH(OAc)3 (1.3 g, 12.06 mmol) and HOAc (0.7 mL, 6.03 mmol). The mixture was heated at 40° C. for 72 h. The reaction was quenched with 2M Na2CO3 and stirred 1 h. The organic layer was collected, dried over MgSO4 and concentrated in vacuo. This crude compound was purified by chromatography on silica gel. Elution with hexane:acetone mixture (90:10) gave a light yellow solid. MS m/z: 269.2 (M+H). Calc'd. for C12H17BrN2-268.06.

Workup

  1. customThe reaction was quenched with 2M Na2CO3
  2. customThe organic layer was collected
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThis crude compound was purified by chromatography on silica gel
  6. washElution with hexane
  7. customacetone mixture (90:10) gave a light yellow solid

Sources & evidence

ORD record
ord-1a7f9b0228e34780bf0f48e591897bec
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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