N-Iodosuccinimide → HCID 90409002, compound

HRID 2177596Notes

Reaction equation

HRID 2177596 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][C:17]2[CH:20]=[N:21][NH:22][C:16]=2[CH2:15]1)=[O:13].[I:23]N1C(=O)CCC1=O>CN(C=O)C>[Cl:1][C:2]1[C:7]([C:8]([F:9])([F:11])[F:10])=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][C:17]2[C:20]([I:23])=[N:21][NH:22][C:16]=2[CH2:15]1)=[O:13]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 90410567HCID 90410567, compound

Product 1

HCID 90409002HCID 90409002, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine (63 mg, 0.191 mmol) in DMF (1 mL) was added N-iodosuccinimide (47 mg, 0.210 mmol). The reaction was allowed to stir for 2 h at rt then poured into ice water (10 mL). The product was extracted with EtOAc three times. The organic layers were combined, dried over anhydrous MgSO4, filtered and concentrated. Chromatography on silica gel (0-50% ethyl acetatehexanes) provided the desired product (48 mg, 55%). MS (ESI) mass calcd. C14H10ClF31N3O, 454.95. m/z found, 455.9 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.27 (br s, 1H), 7.81-7.74 (m, 1H), 7.52-7.43 (m, 2H), 5.13 (d, J=16.7 Hz, 0.6H), 4.82 (d, J=16.7 Hz, 0.6H), 4.47 (d, J=16.0 Hz, 0.4H), 4.37 (d, J=16.0 Hz, 0.4H), 4.27-4.19 (m, 0.4H), 3.95-3.85 (m, 0.4H), 3.45-3.50 (m, 1.2H), 2.62-2.66 (m, 0.8H), 2.51 (m, 0.6H), 2.46-2.37 (m, 0.6H).

Workup

  1. extractionThe product was extracted with EtOAc three times
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-415fa8d9e7a145838fcdd55b69f9323c
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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