Selectfluor → HCID 86722838, compound

HRID 1778732Notes

Reaction equation

HRID 1778732 reaction equation
[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+]([F:21])(CC2)C1.[F:22][C:23]1[C:28]([O:29][CH3:30])=[CH:27][C:26]([O:31][CH3:32])=[CH:25][C:24]=1[C:33]1[N:38]=[CH:37][C:36]2[C:39]([I:48])=[N:40][N:41]([CH:42]3[CH2:47][CH2:46][CH2:45][CH2:44][O:43]3)[C:35]=2[CH:34]=1>C(#N)C>[F:22][C:23]1[C:28]([O:29][CH3:30])=[CH:27][C:26]([O:31][CH3:32])=[C:25]([F:21])[C:24]=1[C:33]1[N:38]=[CH:37][C:36]2[C:39]([I:48])=[N:40][N:41]([CH:42]3[CH2:47][CH2:46][CH2:45][CH2:44][O:43]3)[C:35]=2[CH:34]=1

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 867228616-(2-fluoro-3,5-dimethoxyphenyl)-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 86722838HCID 86722838, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(Chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane ditetrafluoroborate (97 mg, 0.27 mmol) was added a stirring solution of 6-(2-fluoro-3,5-dimethoxyphenyl)-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine (88 mg, 0.18 mmol) in acetonitrile (5 mL). The mixture was stirred at r.t. for 1 h then concentrated. The solid was filtered out and the filtrate was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (30 mg). LCMS (M+H)+=502.0.

Workup

  1. concentrationthen concentrated
  2. filtrationThe solid was filtered out
  3. customthe filtrate was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record
ord-28be45663c0741ee89ef5d0c4e39b7c7
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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