tert-butyl 4-(2-fluoro-4-(3-(1-phenethyl-1H-pyrazol-3-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-3-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 531844Notes

Reaction equation

HRID 531844 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:21]=[CH:20][N:19]([CH2:22][CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[N:18]=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>C(O)(C(F)(F)F)=O.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[CH:21]=[CH:20][N:19]([CH2:22][CH2:23][C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=5)[N:18]=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

3

Reactant 1

HCID 136960277tert-butyl 4-(2-fluoro-4-(3-(1-phenethyl-1H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate

Product 1

HCID 1364926815-(3-fluoro-4-(piperidin-4-yl)phenyl)-3-(1-phenethyl-1H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridineYield 42.6%

Reagents, catalysts & solvents 1

HCID 69846924Toluene trifluoroacetic acidSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(2-fluoro-4-(3-(1-phenethyl-1H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (66 mg, 0.116 mmol) was deprotected in TFA/toluene (5/5 mL) to afford 23 mg (34% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.82-8.81 (d, 1H), 8.58 (s, 1H), 7.87 (s, 1H), 7.58-7.45 (m, 4H), 7.23-7.11 (m, 5H), 6.577-6.570 (d, 1H), 4.48-4.44 (t, 2H), 3.56-3.52 (d, 2H), 3.24-3.15 (m, 5H), 2.15-2.03 (m, 4H). MS: m/z=466.5 (M+1), HPLC: 96.98% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-46415daed35942f4b8a26be31a03ad82
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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