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

HRID 531848Notes

Reaction equation

HRID 531848 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:40]=[C:41]([F:43])[CH:42]=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)=[C:22]([F:39])[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>[F:1][C:2]1[CH:3]=[C:4]([CH:40]=[C:41]([F:43])[CH:42]=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][NH:29][CH2:28][CH2:27]5)=[C:22]([F:39])[CH:21]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1

Participants

3

Reactant 1

HCID 118524096tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-fluorophenyl)piperidine-1-carboxylate

Product 1

HCID 900307553-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-5-(3-fluoro-4-(piperidin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridineYield 28.3%

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-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-fluorophenyl)piperidine-1-carboxylate (64 mg, 0.109 mmol) was deprotected in TFA/toluene (5/5 mL) to afford 14.9 mg (28.3% yield) of the titled compound after purification by preparative TLC using 6% methanol in chloroform as eluent. 1H NMR (CD3OD, 300 MHz): δ 8.48-8.47 (d, 1H), 8.38-8.37 (d, 1H), 8.25 (s, 1H), 7.96 (s, 1H), 7.66 (s, 1H), 7.53-7.39 (m, 3H), 6.92-6.86 (m, 3H), 5.44 (s, 2H), 3.24-3.20 (d, 2H), 3.09-3.07 (m, 1H), 2.87-2.80 (td, 2H), 1.89-1.77 (m, 4H). MS: m/z=488.3 (M+1), HPLC: 95.30% in method A.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-759dc24e887d40fabdec34bec4285e97
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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