Trimethylsilyl iodide → HCID 59006343, compound

HRID 2378979Notes

Reaction equation

HRID 2378979 reaction equation
C[O:2][C:3]1[N:8]=[C:7]2[CH:9]=[CH:10][N:11]([CH3:12])[C:6]2=[CH:5][C:4]=1[CH:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1.[Si](I)(C)(C)C>C(Cl)Cl>[CH3:12][N:11]1[C:6]2[CH:5]=[C:4]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:3](=[O:2])[NH:8][C:7]=2[CH:9]=[CH:10]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 59006361HCID 59006361, compound

Product 1

HCID 59006343HCID 59006343, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To tert-butyl 4-(5-methoxy-1-methyl-1H-pyrrolo [3,2-b]pyridin-6-yl)piperidine-1-carboxylate (104 mg, 0.301 mmol) in CH2Cl2 (3 mL) was added TMS-I (123 μl, 0.903 mmol) at rt. The resulting brown solution was stirred at 60° C. over night. Partial of the solvent was removed on rotary vacuo, the residue was purified on reverse phase PrepHPLC to afford the expected product, 1-methyl-6-(piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridin-5(4H)-one (65 mg, 94%). 1H-NMR (400 MHz, MeOD) δ ppm 2.05 (s, 3 H) 2.13 (s, 3 H) 3.20 (s, 4 H) 3.55 (s, 3 H) 6.25 (s, 1 H) 7.35 (s, 1 H) 8.01 (s, 1 H); Mass spec 232.19 Calc for C13H17N3O 231.14.

Workup

  1. customPartial of the solvent was removed on rotary vacuo
  2. customthe residue was purified on reverse phase PrepHPLC

Sources & evidence

ORD record
ord-175bd98b3e3e47a1a3f5507f7ccb0fa6
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

Loading…