Sodium Carbonate → HCID 90031144, compound

HRID 531557Notes

Reaction equation

HRID 531557 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]4)=[CH:13][CH:12]=3)[CH:9]=2)[N:4]([S:30]([C:33]2[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[CH:3]=1.[CH3:40][C:41]1[C:45](B2OC(C)(C)C(C)(C)O2)=[C:44]([CH3:55])[N:43]([CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([CH3:63])[CH:58]=2)[N:42]=1.C(=O)([O-])[O-].[Na+].[Na+]>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].C1(C)C=CC=CC=1.C(O)C.O>[CH3:40][C:41]1[C:45]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:16]=[CH:15][C:14]([N:17]5[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]5)=[CH:13][CH:12]=4)[CH:9]=3)[N:4]([S:30]([C:33]3[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[CH:3]=2)=[C:44]([CH3:55])[N:43]([CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([CH3:63])[CH:58]=2)[N:42]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 90030611tert-butyl 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate2×HCID 90031404HCID 90031404, compound2×

Product 1

HCID 90031144HCID 90031144, compoundYield 30.8%

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)piperazine-1-carboxylate (intermediate 41) (300 mg, 0.4 mmol) was coupled with (Intermediate 56A) 3,5-dimethyl-1-(3-methylbenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (163 mg, 0.5 mmol) in sodium carbonate (147 mg, 1.0 mmol), PdCl2(dppf) (17 mg, 0.02 mmol), toluene/ethanol/water (2/2/3 ml) to give 90 mg (28% yield) of titled compound.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-48c54af185724e7886acf04a6e7c0330
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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