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

HRID 531855Notes

Reaction equation

HRID 531855 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[N: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[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1

Participants

3

Reactant 1

HCID 90033905tert-butyl 4-(2-fluoro-4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate

Product 1

HCID 900313865-(3-fluoro-4-(piperazin-1-yl)phenyl)-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 93%

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)piperazine-1-carboxylate (80 mg, 0.140 mmol) was deprotected in TFA/DCM (5/5 ml) to afford 12 mg (93% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.54 (s, 2H), 8.262-8.260 (d, 1H), 7.975-7.973 (d, 1H), 7.74 (s, 1H), 7.59-7.52 (m, 2H), 7.38-7.00 (m, 5H), 5.44 (s, 2H), 3.42-3.40 (m, 8H). MS: m/z=471.2 (M+1), HPLC: 97.06% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-20ef7a97db4745878076ab0ff7139720
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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