tert-butyl 4-(4-(3-(1-(3-methylbenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate → 3-(1-(3-methylbenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 531631Notes

Reaction equation

HRID 531631 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][CH:41]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][C:23]([CH:26]5[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]5)=[CH:22][CH:21]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1>C(O)(C(F)(F)F)=O.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:39]=[CH:40][CH:41]=1)[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[CH:21]=[CH:22][C:23]([CH:26]5[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]5)=[CH:24][CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1

Participants

3

Reactant 1

HCID 118523926tert-butyl 4-(4-(3-(1-(3-methylbenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate

Product 1

HCID 900305153-(1-(3-methylbenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridineYield 27%

Reagents, catalysts & solvents 1

HCID 69846924Toluene trifluoroacetic acidSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-7, tert-butyl 4-(4-(3-(1-(3-methylbenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (108 mg, 0.197 mmol) was deprotected in TFA/toluene (5/5 ml). This afforded 30 mg (27% yield) of the titled. 1H NMR (CD3OD, 300 MHz): δ 8.627-8.622 (d, 1H), 8.56 (s, 1H), 8.20 (s, 1H), 7.94 (s, 1H), 7.75-7.71 (m, 3H), 7.44-7.42 (d, 2H), 7.25-7.20 (t, 1H), 7.13-7.07 (m, 3H), 5.37 (s, 2H), 3.55-3.51 (d, 2H), 3.21-3.13 (m, 2H), 3.03-2.94 (m, 1H), 2.31 (s, 3H), 2.14-2.10 (d, 2H), 2.03-1.89 (qd, 2H). MS: m/z=448.4 (M+1), HPLC: 98.27% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-b39fc2b7c8624e2496a83c71ffa8986a
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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