Sodium Carbonate → tert-butyl 4-(4-(3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate

HRID 531639Notes

Reaction equation

HRID 531639 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[C:10]3[C:16](I)=[CH:15][N:14]([S:18]([C:21]4[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=4)(=[O:20])=[O:19])[C:11]3=[N:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]1.CC1(C)C(C)(C)OB([C:49]2[CH:50]=[N:51][N:52]([CH2:54][C:55]3[CH:56]=[N:57][CH:58]=[CH:59][CH:60]=3)[CH:53]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:57]1[CH:58]=[CH:59][CH:60]=[C:55]([CH2:54][N:52]2[CH:53]=[C:49]([C:16]3[C:10]4[C:11](=[N:12][CH:13]=[C:8]([C:6]5[CH:5]=[CH:4][C:3]([CH:28]6[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])[CH2:30][CH2:29]6)=[CH:2][CH:7]=5)[CH:9]=4)[N:14]([S:18]([C:21]4[CH:22]=[CH:23][C:24]([CH3:25])=[CH:26][CH:27]=4)(=[O:19])=[O:20])[CH:15]=3)[CH:50]=[N:51]2)[CH:56]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 179991853-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyridine2×HCID 90033965tert-butyl 4-(2-fluoro-4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate2×

Product 1

HCID 118524050tert-butyl 4-(4-(3-(1-(pyridin-3-ylmethyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylateYield 72%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Using similar reaction conditions as described in step-i of example-1, tert-butyl 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (intermediate 67B) (200 mg, 0.304 mmol) was coupled with 3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyridine (intermediate 64) (104 mg, 0.364 mmol) using Pd(dppf)Cl2 (11 mg, 0.015 mol) and sodium carbonate (97 mg, 0.912 mmol) in acetonitrile/water (3/1 ml) to afford 150 mg (72.0% yield) of the titled compound after column purification using 3% methanol in DCM as eluent.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-ae09b4981dd1498e8c2f89c85b5f4a1a
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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