tert-butyl 4-(2-fluoro-4-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate → 5-(3-fluoro-4-(piperidin-4-yl)phenyl)-3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 531840Notes

Reaction equation

HRID 531840 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[CH:18]=[N:19][N:20]([CH2:22][CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH:21]=4)=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[CH:30]1[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]1>CO.Cl.O1CCOCC1>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[CH:18]=[N:19][N:20]([CH2:22][CH2:23][C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=5)[CH:21]=4)=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[CH:30]1[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]1

Participants

4

Reactant 1

HCID 118524118tert-butyl 4-(2-fluoro-4-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate

Product 1

HCID 900315525-(3-fluoro-4-(piperidin-4-yl)phenyl)-3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 12.2%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21893726Hydrochloride methanolSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(2-fluoro-4-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (82 mg, 0.145 mmol) was deprotected in methanol/HCl in dioxane (5/5 mL) to afford 8.2 mg (12.2% yield) of the titled compound after purification by preparative TLC using 8% methanol in chloroform as eluent. 1H NMR (CD3OD, 300 MHz): δ 8.448-8.442 (d, 1H), 8.098-8.091 (d, 1H), 7.839-7.837 (d, 1H), 7.73 (s, 1H), 7.54 (s, 1H), 7.48-7.38 (m, 3H), 7.26-7.12 (m, 5H), 7.44-7.41 (t, 2H), 3.37-3.31 (m, 1H), 3.19-3.15 (t, 3H), 3.03-2.93 (td, 2H), 1.97-1.88 (m, 5H). MS: m/z=466.5 (M+1), HPLC: 98.63% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-83729a8afcf3460bbb727f13f1f03a83
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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