5-Amino-2-fluoropyridine → HCID 57986920, compound

HRID 1516516Notes

Reaction equation

HRID 1516516 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:8])=[N:6][CH:7]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([C:22]2[S:23][CH:24]=[C:25]([CH:27]=O)[N:26]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:9]([O:13][C:14]([N:16]1[CH2:17][CH2:18][CH:19]([C:22]2[S:23][CH:24]=[C:25]([CH2:27][NH:1][C:2]3[CH:7]=[N:6][C:5]([F:8])=[CH:4][CH:3]=3)[N:26]=2)[CH2:20][CH2:21]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 8194405-Amino-2-fluoropyridineHCID 5049666Sodium triacetoxyborohydrideHCID 7172298tert-Butyl 4-(4-formyl-1,3-thiazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 57986920HCID 57986920, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-amino-2-fluoropyridine (0.476 g, 4.2 mmol) was added to 4-(4-Formyl-thiazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.84 g, 2.8 mmol) in dry DCM (10 mL). Sodium triacetoxyborohydride (0.9 g, 4.2 mmol) was then added. The reaction was stirred for 3 hours at room temperature under N2. The organic layer was washed with 2M NaOH solution, water, brine, dried (MgSO4), and the solvent was removed in vacuo. The material was purified by silica gel chromatography (DCM/methanol: 10:1 v/v) to give the desired product. 1H NMR (CDCl3): δ 7.59-7.60 (1H, m), 7.06-7.10 (1H, m), 7.02 (1H, s), 6.76 (1H, dd, J=8.8, 3.6 Hz), 4.4 (2H, d), 4.20-4.31 (3H, m), 3.09-3.17 (1H, m), 2.8-2.95 (2H, m), 2.07-2.10 (2H, m), 1.77-1.47, (2H, m), 1.47 (9H, s).

Workup

  1. washThe organic layer was washed with 2M NaOH solution, water, brine
  2. dry with materialdried (MgSO4)
  3. customthe solvent was removed in vacuo
  4. customThe material was purified by silica gel chromatography (DCM/methanol: 10:1 v/v)

Sources & evidence

ORD record
ord-32bb26d891f441cc8d6752828e8af963
Source dataset
uspto-grants-2012_07
Patent number
US08227495B2

Reaction notes

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