tert-butyl 4-(2-fluoro-4-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-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)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 531863Notes

Reaction equation

HRID 531863 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]([CH3:31])=[N:19][N:20]([CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=5)[C:21]=4[CH3:22])=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[CH:32]1[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]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]([CH3:31])=[N:19][N:20]([CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=5)[C:21]=4[CH3:22])=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1

Participants

3

Reactant 1

HCID 90034057tert-butyl 4-(2-fluoro-4-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate

Product 1

HCID 729448565-(3-fluoro-4-(piperidin-4-yl)phenyl)-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 9.8%

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)-3,5-dimethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (110 mg, 0.184 mmol) was deprotected in TFA/DCM (3/0.5 mL) to afford 9 mg (8.1% yield) of the titled compound. 1H NMR (CD3OD, 400 MHz): δ 8.6 (s, 1H), 8.14-8.13 (d, 1H), 7.55 (s, 1H), 7.50-7.30 (m, 4H), 7.05-6.95 (td, 2H), 6.90-6.85 (d, 1H), 5.37 (s, 2H), 3.52-3.49 (d, 2H), 3.24-3.14 (m, 3H), 2.20 (s, 3H), 2.18 (s, 3H), 2.10-1.95 (m, 4H). MS: m/z=497.8 (M+1), HPLC: 96.3% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-b31c66c626a84d878368a5f0d47fd9cd
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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