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

HRID 531467Notes

Reaction equation

HRID 531467 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.CC1(C)C(C)(C)OB([C:30]2[CH:31]=[N:32][N:33]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:45])([F:44])[F:43])[CH:37]=3)[CH:34]=2)O1.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:30]3[CH:31]=[N:32][N:33]([CH2:35][C:36]4[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:44])([F:45])[F:43])[CH:37]=4)[CH:34]=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 710929904-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(3-trifluoromethyl-benzyl)-1H-pyrazole2×

Product 1

HCID 900305735-bromo-1-tosyl-3-(1-(3-(trifluoromethyl)benzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 46.2%

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) (300 mg, 0.629 mmol) was coupled with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(3-(trifluoromethyl)benzyl)-1H-pyrazole (Intermediate 4) (310 mg, 0.88 mmol) in sodium carbonate (200 mg, 1.88 mmol), bis(triphenyl phosphine)palladium(ii) dichloride (22 mg, 0.0314 mmol) and toluene/ethanol/water (30/10/2.5 ml) to afford 167 mg (46.2% yield) of the pure product after column purification using 30% ethyl acetate in hexane as eluent. MS: m/z=577.00 (M+2).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-0572f37e4ff342f5a7813739906dd597
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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