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

HRID 531636Notes

Reaction equation

HRID 531636 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:40]=[CH:41][CH:42]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([CH:27]5[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]5)=[CH:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH:9]=[N:8]1>C(O)(C(F)(F)F)=O.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:40]=[CH:41][CH:42]=1)[CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[CH:23][C:24]([CH:27]5[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]5)=[CH:25][CH:26]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH:9]=[N:8]1

Participants

3

Reactant 1

HCID 118523939tert-butyl 4-(4-(3-(1-(3-methoxybenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate

Product 1

HCID 900313083-(1-(3-methoxybenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridineYield 16.2%

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-methoxybenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (85 mg, 0.150 mmol) was deprotected in TFA/toluene (2.5/5 ml). This afforded 11 mg (16.2% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.458-8.451 (d, 1H), 8.327-8.321 (d, 1H), 8.14 (s, 1H), 7.90 (s, 1H), 7.65-7.61 (m, 3H), 7.38-7.35 (d, 2H), 7.29-7.23 (m, 1H), 6.87-6.85 (m, 2H), 5.38 (s, 2H), 3.25-3.76 (s, 3H), 3.25-3.20 (d, 2H), 2.87-2.73 (m, 3H), 1.93-1.72 (m, 4H). MS: m/z=464.6 (M+1), HPLC: 90.63% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-cf6c93d3dee34cb8a6e5fba9f4517894
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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