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

HRID 2378982Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([Si](C(C)C)(C(C)C)C(C)C)[CH:9]=[CH:10][C:5]2=[C:4]([C:21]2([OH:34])[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]2)[CH:3]=1.[Si](I)(C)(C)C>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[C:4]([C:21]2([OH:34])[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]2)[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To tert-butyl 4-(6-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-4-hydroxypiperidine-1-carboxylate (510 mg, 1.00 mmol) in CH2Cl2 (6 mL) was slowly dropwise added TMS-I (0.43 mL, 3.01 mmol) at rt, and stirred at 60° C. overnight. Partial of the solvent was removed on rotary vacuo, and the residue was purified on reverse phase PrepHPLC to afford the expected product, 4-(6-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-4-ol (310 mg, 63%), as a dark brown solid. 1H-NMR (400 MHz, CHLOROFORM-D) δ ppm 2.02 (d, J=14.35 Hz, 2 H) 2.65-2.76 (m, 2 H) 3.42 (d, J=11.33 Hz, 2 H) 3.58 (d, J=11.83 Hz, 2 H) 4.61 (s, 2 H) 6.91 (d, J=3.53 Hz, 1 H) 7.13 (s, 1 H) 7.28 (d, J=3.53 Hz, 1 H); Mass spec. 252.05 (MH+) calc. for C12H14ClN3O 251.08.

Workup

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

Sources & evidence

ORD record: ord-5c4a1b800dab4b1b881179bb517f1c71
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470680B2

Reaction notes

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