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

HRID 531628Notes

Reaction equation

HRID 531628 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][C:23]5[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=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>C(O)(C(F)(F)F)=O.C(Cl)Cl>[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][C:23]5[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=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][NH:33][CH2:32][CH2:31]1

Participants

3

Reactant 1

HCID 118523873tert-butyl 4-(2-fluoro-4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate

Product 1

HCID 729443275-(3-fluoro-4-(piperidin-4-yl)phenyl)-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 19.6%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(2-fluoro-4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (150 mg, 0.263 mmol) was deprotected in TFA/DCM (2/5 ml). This afforded 30 mg (19.6% yield) of the titled. 1H NMR (CD3OD, 400 MHz): δ 8.67-8.66 (d, 1H), 8.60 (s, 1H), 8.28 (s, 1H), 7.97 (s, 1H), 7.78 (s, 1H), 7.58-7.54 (m, 2H), 7.47-7.43 (t, 1H), 7.39-7.33 (q, 1H), 7.12-7.10 (d, 1H), 7.05-7.00 (m, 2H), 5.43 (s, 2H), 3.55-3.52 (d, 2H), 3.28-3.16 (m, 3H), 2.21-2.03 (m, 4H). MS: m/z=470.4 (M+1), HPLC: 98.34% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-f1441bf576a14ed6a03f19752f111069
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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