3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine → 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(1-methylpiperidin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 531625Notes

Reaction equation

HRID 531625 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=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]([C:26]5[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH:31]=5)=[CH:22][CH:21]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1>COC1C=CC(CN2C=C(B3OC(C)(C)C(C)(C)O3)C=N2)=CC=1.[OH-].[Pd+2].[OH-]>[F:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=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][N:29]([CH3:32])[CH2:30][CH2:31]5)=[CH:24][CH:25]=4)[CH:18]=3)[NH:13][CH:12]=2)[CH:8]=[N:7]1

Participants

4

Reactant 1

HCID 1185240283-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 900314733-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(1-methylpiperidin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridineYield 7.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 534402131-(4-methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-82, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)phenyl)-1H-pyrrolo[2,3-b]pyridine (130 mg, 0.280 mmol) was reduced with palladium hydroxide (50 mg) in ethyl acetate/ethanol 5/5 mL to afford 10 mg (6.0% yield) of the titled compound. 1H NMR (CD3OD, 300 MHz): δ 8.627-8.621 (d, 1H), 8.56 (s, 1H), 8.26 (s, 1H), 7.97 (s, 1H), 7.77-7.73 (m, 3H), 7.45-7.42 (d, 2H), 7.38-7.33 (m, 1H), 7.13-7.00 (m, 3H), 5.44 (s, 2H), 3.67-3.63 (d, 2H), 3.22-3.15 (t, 2H), 3.03-2.94 (m, 4H), 2.20-2.00 (m, 4H). MS: m/z=466.7 (M+1), HPLC: 95.92% in method B.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-ddecddc713fb4e1c82885a0ffcd6bc60
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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