Sodium Carbonate → 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-N-methylbenzenesulfonamide

HRID 531505Notes

Reaction equation

HRID 531505 reaction equation
FC1C=CC=CC=1CN1C=C(C2C3C(=NC=C(C4C=C(NS(C)(=O)=O)C=CC=4)C=3)NC=2)C=N1.I[C:35]1[C:43]2[C:38](=[N:39][CH:40]=[C:41]([C:44]3[CH:45]=[CH:46][C:47]([O:55][CH3:56])=[C:48]([S:50]([NH:53][CH3:54])(=[O:52])=[O:51])[CH:49]=3)[CH:42]=2)[N:37]([S:57]([C:60]2[CH:66]=[CH:65][C:63]([CH3:64])=[CH:62][CH:61]=2)(=[O:59])=[O:58])[CH:36]=1.[F:67][C:68]1[CH:69]=[C:70]([CH:88]=[C:89]([F:91])[CH:90]=1)[CH2:71][N:72]1[C:76]([CH3:77])=[C:75](B2OC(C)(C)C(C)(C)O2)[C:74]([CH3:87])=[N:73]1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O>[F:67][C:68]1[CH:69]=[C:70]([CH:88]=[C:89]([F:91])[CH:90]=1)[CH2:71][N:72]1[C:76]([CH3:77])=[C:75]([C:35]2[C:43]3[C:38](=[N:39][CH:40]=[C:41]([C:44]4[CH:45]=[CH:46][C:47]([O:55][CH3:56])=[C:48]([S:50]([NH:53][CH3:54])(=[O:52])=[O:51])[CH:49]=4)[CH:42]=3)[N:37]([S:57]([C:60]3[CH:66]=[CH:65][C:63]([CH3:64])=[CH:62][CH:61]=3)(=[O:59])=[O:58])[CH:36]=2)[C:74]([CH3:87])=[N:73]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 72944747N-(3-(3-(1-(2-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamideHCID 900300305-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy-N-methylbenzenesulfonamide2×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 1185238865-(3-(1-(3,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy-N-methylbenzenesulfonamideYield 77.9%

Reagents, catalysts & solvents 1

HCID 86587398Ethanol toluene waterSolvent

Procedure

Using similar reaction conditions as described in step-ii of example 1, 5-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxy-N-methylbenzenesulfonamide (intermediate 22) (200 mg, 0.335 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) (146 mg, 0.418 mmol) in sodium carbonate (100 mg, 1.0 mmol) Pd(PPh3)2Cl2 (11.7 mg, 0.011 mmol), Toluene/ethanol/water (20/10/2 ml) to afford 180 mg (77.9% yield) of the titled compound after purification by column (SiO2-eluted by 0.4 to 1.2% MeOH in CHCl3). MS: m/z=692.0 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-448bf63873c74812a34ec89de70960c9
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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