Sodium Carbonate → HCID 118524033, compound

HRID 531851Notes

Reaction equation

HRID 531851 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:60]=[CH:59][N:58]=[CH:57][CH:56]=3)[CH:53]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)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:58]1[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:7]=[CH:2][C:3]([CH:28]6[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[CH2:32][CH2:33]6)=[CH:4][CH:5]=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:20])=[O:19])[CH:15]=3)[CH:50]=[N:51]2)=[CH:56][CH:57]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 177499264-{[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 118524033HCID 118524033, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

Using similar reaction conditions as described in step-ii 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) (150 mg, 0.52 mmol) was coupled with 4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)pyridine (intermediate 64G) (180 mg, 0.63 mmol) using sodium carbonate (165 mg, 1.56 mmol) and Pd(dppf)Cl2 (18 mg, 0.026 mmol) in toluene/ethanol/water (10/10/2 mL) to afford 142 mg (crude) of the titled compound. MS: m/z=589.4 (M-Boc+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-12d014a821964508a001e4f2aa556a8a
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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