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

HRID 531836Notes

Reaction equation

HRID 531836 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[C:18]([CH3:30])=[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:31]1[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]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[C:18]([CH3:30])=[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:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1

Participants

3

Reactant 1

HCID 118524014tert-butyl 4-(2-fluoro-4-(3-(1-(3-fluorobenzyl)-3-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate

Product 1

HCID 900334845-(3-fluoro-4-(piperidin-4-yl)phenyl)-3-(1-(3-fluorobenzyl)-3-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 21.6%

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)-3-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (140 mg, 0.239 mmol) was deprotected in TFA/DCM (5/1 mL) to afford 25 mg (17.48% yield) of the titled compound after purification by preparative HPLC along with one more isomer 1H NMR (CD3OD, 300 MHz): δ 8.70-8.60 (bs, 1H), 8.59 (s, 1H), 8.20 (s, 1H), 7.70 (s, 1H), 7.60-7.30 (m, 4H), 7.20-6.95 (m, 3H), 5.37 (s, 2H), 3.60-3.50 (m, 2H), 3.30-3.10 (m, 3H), 2.40 (s, 3H), 2.15-2.00 (m, 4H). MS: m/z=484.4 (M+1), HPLC: 98.76% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-79f8a7ac92e446448ed5a77cc0932a69
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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