Sodium Carbonate → N-(3-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-dimethoxy phenyl)methanesulfonamide

HRID 531521Notes

Reaction equation

HRID 531521 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[C:12]([O:24][CH3:25])=[C:13]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)[CH:9]=2)[N:4]([S:26]([C:29]2[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH:3]=1.[F:36][C:37]1[CH:38]=[C:39]([CH:57]=[CH:58][CH:59]=1)[CH2:40][N:41]1[C:45]([CH3:46])=[C:44](B2OC(C)(C)C(C)(C)O2)[C:43]([CH3:56])=[N:42]1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1.C(O)C.O>[F:36][C:37]1[CH:38]=[C:39]([CH:57]=[CH:58][CH:59]=1)[CH2:40][N:41]1[C:45]([CH3:46])=[C:44]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[C:12]([O:24][CH3:25])=[C:13]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:14]([O:17][CH3:18])=[CH:15][CH:16]=4)[CH:9]=3)[N:4]([S:26]([C:29]3[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[CH:3]=2)[C:43]([CH3:56])=[N:42]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 900306711-(3-Fluoro-benzyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazoleHCID 90031006N-(3-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-dimethoxyphenyl) methane sulfonamide2×

Product 1

HCID 90030283N-(3-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-dimethoxy phenyl)methanesulfonamideYield 64.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-1, N-(3-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-dimethoxyphenyl) methane sulfonamide (intermediate 34) (55 mg, 0.485 mmol) was coupled with 1-(3-fluorobenzyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate-16) (57.8 mg, 0.175 mmol) in sodium carbonate (28 mg, 0.263 mmol), Pd(PPh3)2Cl2 (3.0 mg, 0.0043 mmol), Toluene/ethanol/water (10/5/2 ml) to give 40 mg (64.5% yield) of titled compound. MS: m/z=704.2 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-404c44ce61394699905ffaa074d20389
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…