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

HRID 531469Notes

Reaction equation

HRID 531469 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.[CH3:22][O:23][C:24]1[CH:44]=[CH:43][C:27]([CH2:28][N:29]2[CH:33]=[C:32](B3OC(C)(C)C(C)(C)O3)[CH:31]=[N:30]2)=[CH:26][CH:25]=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:32]3[CH:31]=[N:30][N:29]([CH2:28][C:27]4[CH:43]=[CH:44][C:24]([O:23][CH3:22])=[CH:25][CH:26]=4)[CH:33]=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 534402131-(4-methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×

Product 1

HCID 1185239695-bromo-3-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineYield 57.95%

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) (750 mg, 1.78 mmol) was coupled with 1-(4-methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Intermediate 5) (671 mg, 2.13 mmol) in sodium carbonate (614 mg, 4.4 mol), bis(triphenyl phosphine)palladium(ii) dichloride (62 mg, 2.13 mmol) and toluene/ethanol/water (10/10/5 ml) to afford 550.0 mg (57.95% yield) of the pure product after column purification using 30% ethyl acetate in hexane as eluent. 1H NMR (DMSO-d6, 300 MHz): δ 8.56-8.50 (m, 3H), 8.25 (s, 1H), 8.08 (s, 1H), 7.97-7.94 (d, 2H), 7.41-7.39 (d, 2H), 7.27-7.24 (d, 2H), 6.91-6.89 (d, 2H), 5.27 (s, 2H), 3.72 (s, 3H), 2.32 (s, 3H). MS: m/z=539.0 (M+2).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-f0f5d5dcf8cc40439d55742231a27c82
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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