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

HRID 531638Notes

Reaction equation

HRID 531638 reaction equation
[CH2:1]([N:9]1[CH:13]=[C:12]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([C:23]4[CH:28]=[CH:27][C:26]([CH:29]5[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]5)=[CH:25][CH:24]=4)[CH:21]=3)[NH:16][CH:15]=2)[CH:11]=[N:10]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)(C(F)(F)F)=O.C1(C)C=CC=CC=1>[CH2:1]([N:9]1[CH:13]=[C:12]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([C:23]4[CH:24]=[CH:25][C:26]([CH:29]5[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]5)=[CH:27][CH:28]=4)[CH:21]=3)[NH:16][CH:15]=2)[CH:11]=[N:10]1)[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 118523910tert-butyl 4-(4-(3-(1-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate

Product 1

HCID 900648123-(1-phenethyl-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridineYield 20.2%

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-phenethyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (85 mg, 0.155 mmol) was deprotected in TFA/toluene (2.5/5 ml). This afforded 14 mg (20.2% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.576-8.571 (d, 1H), 8.46-8.45 (d, 1H), 7.90 (s, 1H), 7.81 (s, 1H), 7.73-7.71 (m, 3H), 7.48-7.46 (d, 2H), 7.25-7.20 (m, 2H), 7.14-7.07 (m, 3H), 7.48-7.43 (t, 2H), 3.56-3.52 (d, 2H), 3.22-3.15 (m, 4H), 3.07-2.98 (dt, 1H), 2.17-2.13 (d, 2H), 2.06-1.91 (m, 2H). MS: m/z=448.4 (M+1), HPLC: 91.78% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-f58e2ce028d1481cb32eaef3b0c07b00
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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