Trimethylsilyl iodide → 6-(piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridin-5(4H)-one

HRID 2378976Notes

Reaction equation

C[O:2][C:3]1[N:8]=[C:7]2[CH:9]=[CH:10][N:11]([Si](C(C)C)(C(C)C)C(C)C)[C:6]2=[CH:5][C:4]=1[CH:22]1[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]1.[Si](I)(C)(C)C>C(Cl)Cl>[NH:25]1[CH2:24][CH2:23][CH:22]([C:4]2[C:3](=[O:2])[NH:8][C:7]3[CH:9]=[CH:10][NH:11][C:6]=3[CH:5]=2)[CH2:27][CH2:26]1

Participants

Conditions

Temperature: 60 °C

Procedure

To tert-butyl 4-(5-methoxy-1-(triisopropylsilyl)-1H-pyrrolo [3,2-b]pyridin-6-yl)piperidine-1-carboxylate (130 mg, 0.267 mmol) in CH2Cl2 (3 mL) was added TMS-I (163 μl, 1.20 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, 6-(piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridin-5(4H)-one (49.3 mg, 85%). 1H-NMR (400 MHz, MeOD) δ ppm 1.85 (dd, J=12.84, 3.53 Hz, 2 H) 2.12 (d, J=14.10 Hz, 3 H) 3.06-3.18 (m, 4 H) 3.42-3.52 (m, 3 H) 6.14 (t, J=2.14 Hz, 1 H) 7.20 (dt, J=2.96, 1.42 Hz, 1 H) 7.62 (s, 1 H); Mass spec 218.14 (MH+), Calc for C12H15N3O 217.12.

Workup

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

Sources & evidence

ORD record: ord-12b05f45a4684cfcbe58374187e38307
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470680B2

Reaction notes

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