Selectfluor → HCID 86656451, compound

HRID 1028050Notes

Reaction equation

HRID 1028050 reaction equation
F[B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+]([F:21])(CC1)CC2.[Cl:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][N:32]=1)[N:29]=[CH:28][CH:27]=[C:26]2[N:33]1[CH2:38][CH2:37][CH2:36][C@H:35]([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH2:34]1>CC#N>[Cl:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][N:32]=1)[N:29]=[CH:28][C:27]([F:21])=[C:26]2[N:33]1[CH2:38][CH2:37][CH2:36][C@H:35]([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:43])([CH3:45])[CH3:44])[CH2:34]1

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 86656450HCID 86656450, compound

Product 1

HCID 86656451HCID 86656451, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (1.0 equiv.) was added to a solution of (S)-tert-butyl 1-(6-chloro-1,7-naphthyridin-4-yl)piperidin-3-ylcarbamate (1.0 equiv.) in MeCN (0.14 M). After stirring for 18 hours, Na2CO3(sat.) was added to quench. The solution was partitioned between EtOAc and Na2CO3(sat.) washed further with NaCl(sat.), dried over MgSO4, concentrated and purified by silica gel chromatography (25-50-100% EtOAc/hexanes w/0.1% DIEA eluant) to yield (S)-tert-butyl 1-(6-chloro-3-fluoro-1,7-naphthyridin-4-yl)piperidin-3-ylcarbamate (15%), as well as recovered (S)-tert-butyl 1-(6-chloro-1,7-naphthyridin-4-yl)piperidin-3-ylcarbamate (55%). LCMS (m/z): 381.1/383.0 (MH+); LC Rt=4.20 min.

Workup

  1. customto quench
  2. customThe solution was partitioned between EtOAc and Na2CO3(sat.)
  3. washwashed further with NaCl(sat.)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (25-50-100% EtOAc/hexanes w/0.1% DIEA eluant)

Sources & evidence

ORD record
ord-1db9ed2892534052aade92648ce3253c
Source dataset
uspto-grants-2014_05
Patent number
US08735424B2

Reaction notes

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