Potassium Carbonate → HCID 70952154, compound

HRID 63597Notes

Reaction equation

HRID 63597 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([Br:11])[CH:9]=2)[N:4]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:3]=1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.C(O)C>[C:21]1([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([Br:11])[CH:9]=3)[N:4]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:3]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 242292401-Benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 70952154HCID 70952154, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3-iodo-5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (250 mg, 0.54 mmol) in a 3:1 toluene/ethanol mixture (17 ml) are added benzene boronic acid (65 mg, 0.54 mmol), K2CO3 (1.6 ml of 2 M solution in water, 3.20 mmol) and Pd(PPh3)4 (1.5 mol %) and the reaction is heated at 110° C. for 3.5 hours under argon.

Sources & evidence

ORD record
ord-61dfe940b77f4133ba5518c354d86172
Source dataset
uspto-grants-2016_09
Patent number
US09447093B2

Reaction notes

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