3-Aminoisonicotinaldehyde → HCID 68243919, compound

HRID 588406Notes

Reaction equation

HRID 588406 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=O.Cl.[F:11][C:12]1([F:17])[CH2:16][CH2:15][NH:14][CH2:13]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CO>[F:11][C:12]1([F:17])[CH2:16][CH2:15][N:14]([CH2:8][C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[NH2:1])[CH2:13]1

Participants

6

Reactant 3

HCID 27630013-AminoisonicotinaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 249034823,3-Difluoropyrrolidine hydrochloride

Product 1

HCID 68243919HCID 68243919, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

3-Amino-pyridine-4-carbaldehyde (250 mg, 2.05 mmol) was dissolved in DCM (4 mL) and MeOH (4 mL), and 3,3-difluoropyrrolidine hydrochloride (353 mg, 2.46 mmol) and NaBH(OAc)3 (521 mg, 2.46 mmol) were added. The reaction mixture was stirred for 18 h, quenched with water (5 mL) and the solvents were removed in vacuo. The residue was dissolved in DCM (20 mL) and washed with sat aq Na2CO3 (5 mL). The aqueous phase was extracted with DCM (3×20 mL) and the combined organic fractions were dried (MgSO4) and concentrated in vacuo to give the crude title compound as a yellow gum (246 mg, 56%). LCMS (ES+): 214.0 (M+H)+.

Workup

  1. customquenched with water (5 mL)
  2. customthe solvents were removed in vacuo
  3. dissolutionThe residue was dissolved in DCM (20 mL)
  4. washwashed
  5. extractionThe aqueous phase was extracted with DCM (3×20 mL)
  6. dry with materialthe combined organic fractions were dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf5b6fb9e2b2478a96a0d9d3b91c2996
Source dataset
uspto-grants-2016_01
Patent number
US09227967B2

Reaction notes

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