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

HRID 531502Notes

Reaction equation

HRID 531502 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([O:22][CH3:23])=[C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:16]=3)[CH:9]=2)[N:4]([S:24]([C:27]2[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH:3]=1.[F:34][C:35]1[CH:36]=[C:37]([CH:55]=[C:56]([F:58])[CH:57]=1)[CH2:38][N:39]1[C:43]([CH3:44])=[C:42](B2OC(C)(C)C(C)(C)O2)[C:41]([CH3:54])=[N:40]1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O>[F:34][C:35]1[CH:36]=[C:37]([CH:55]=[C:56]([F:58])[CH:57]=1)[CH2:38][N:39]1[C:43]([CH3:44])=[C:42]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:12]=[CH:13][C:14]([O:22][CH3:23])=[C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:16]=4)[CH:9]=3)[N:4]([S:24]([C:27]3[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH:3]=2)[C:41]([CH3:54])=[N:40]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 90030027N-(5-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamide2×HCID 900312201-(3,5-Difluoro-benzyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole2×

Product 1

HCID 90031127N-(5-(3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy phenyl) methanesulfonamideYield 113.7%

Reagents, catalysts & solvents 1

HCID 86587398Ethanol toluene waterSolvent

Procedure

Using similar reaction conditions as described in step-ii of example-1, N-(5-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamide (Intermediate 23) (160 mg, 0.267 mmol) was coupled with 1-(3,5-difluorobenzyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 24) (111.89 mg, 0.321 mmol) in sodium carbonate (84.89 mg, 0.801 mmol) Pd(PPh3)2Cl2 (9.7 mg, 0.013), Toluene/ethanol/water (7/7/2 mL) to afford 210 mg of the crude compound. MS: m/z=692.1 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-b66389684c784e51a09b267045093b4e
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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