N-Iodosuccinimide → HCID 178519550, compound

HRID 1865580Notes

Reaction equation

HRID 1865580 reaction equation
[N:1]1([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:16]=[C:17]4[CH:23]=[N:22][NH:21][C:18]4=[N:19][CH:20]=3)[CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[I:24]N1C(=O)CCC1=O>ClC(Cl)C.ClCCl>[I:24][C:23]1[C:17]2[C:18](=[N:19][CH:20]=[C:15]([C:11]3[CH:10]=[C:9]([C:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)=[O:8])[CH:14]=[CH:13][CH:12]=3)[CH:16]=2)[NH:21][N:22]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 59836109morpholin-4-yl-[3-(1H-pyrazolo[3,4-b]pyridin-5-yl)-phenyl]-methanone

Product 1

HCID 178519550HCID 178519550, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Morpholin-4-yl-[3-(1H-pyrazolo[3,4-b]pyridin-5-yl)-phenyl]-methanone (2.30 g, 80% pure, ˜6 mmol) and of N-iodosuccinimide (2.50 g, 1.1 mmol) were dissolved in dichloroethane (180 mL). The mixture was stirred under reflux conditions for 5 h, then cooled to room temperature and diluted with dichloromethane. The solution was washed with saturated aqueous solution of sodium thiosulfate (1×) and then with a saturated aqueous solution of sodium bromide(2×), dried over sodium sulfate, filtered and concentrated. The resulting residue was washed with ether (80 mL) and dried to afford [3-(3-iodo-1H-pyrazolo[3,4-b]pyridin-5-yl)-phenyl]-morpholin-4-yl-methanone as a beige powder (2.881 g, 88% yield over two steps). 1H-NMR (500 MHz, d6-DMSO) δ 14.19 (s, 1H), 8.92 (d, 1H), 8.14 (d, 1H), 7.91 (m, 1H), 7.83 (m, 1H), 7.59 (ddd, 1H), 7.44 (dt, 1H), 3.75-3.35 (m, 8H).

Workup

  1. washThe solution was washed with saturated aqueous solution of sodium thiosulfate (1×)
  2. dry with materialwith a saturated aqueous solution of sodium bromide(2×), dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washThe resulting residue was washed with ether (80 mL)
  6. customdried

Sources & evidence

ORD record
ord-d868cc227b7c40dab1e21c7948abfc77
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

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