N-Iodosuccinimide → tert-butyl 4-(2-fluoro-4-(3-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate

HRID 531456Notes

Reaction equation

HRID 531456 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]3[CH:16]=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1.[I:30]N1C(=O)CCC1=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:16]([I:30])=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 90030541tert-butyl 4-(2-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate

Product 1

HCID 118524041tert-butyl 4-(2-fluoro-4-(3-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylateYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using similar reaction conditions as described in step i of intermediate 1, tert-butyl 4-(2-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (320 mg, 0.810 mmol) was iodinated with N-iodosuccinimide (219 mg, 0.972 mmol) in DCM (20 ml) to afford 400 mg (94.7% yield) of the pure product. MS: m/z=522.1 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-081d3248fbf840f3bf77f198564fdbe6
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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