Sodium Carbonate → 5-bromo-3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 531472Notes

Reaction equation

HRID 531472 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1.[F:22][C:23]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][C:24]=1[CH2:25][N:26]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[N:27]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>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:29]3[CH:28]=[N:27][N:26]([CH2:25][C:24]4[CH:40]=[C:41]([F:44])[CH:42]=[CH:43][C:23]=4[F:22])[CH:30]=3)=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 497590665-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 894980241H-Pyrazole, 1-[(2,5-difluorophenyl)methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2×

Product 1

HCID 1185239635-bromo-3-(1-(2,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineYield 42.63%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

Using similar reaction conditions as described in step-i of example 1,5-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine (Intermediate 1) (1 g, 2.37 mmol) was coupled with 1-(2,5-difluorobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Intermediate 6) (688 mg, 3.3 mmol) in sodium carbonate (749 mg, 7.07 mmol), bis(triphenyl phosphine)palladium(ii) dichloride (83 mg, 0.11 mmol) and toluene/ethanol/water (10/10/5 ml) to afford 550 mg (42.63% yield) of the pure product after column purification using 30% ethyl acetate in hexane as eluent. 1H NMR (DMSO-d6, 300 MHz): δ 8.59-8.51 (m, 3H), 8.29 (s, 1H), 8.13 (s, 1H), 7.98-7.95 (d, 2H), 7.42-7.40 (d, 2H), 7.35-7.10 (m, 4H), 5.52 (s, 2H), 2.33 (s, 3H). MS: m/z=542.6 (M−1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-58d0b1dac6a54491b9492713184418d5
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

Loading…