Potassium Carbonate → HCID 58532461, compound

HRID 1404603Notes

Reaction equation

HRID 1404603 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:10]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH3:24][N:25]1[C:33]2[C:28](=[CH:29][C:30](B(O)O)=[CH:31][CH:32]=2)[CH:27]=[CH:26]1>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.CN(C=O)C>[CH3:24][N:25]1[C:33]2[C:28](=[CH:29][C:30]([C:2]3[CH:3]=[C:4]4[N:10]([O:11][C:12]5[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=5)[CH:9]=[CH:8][C:5]4=[N:6][CH:7]=3)=[CH:31][CH:32]=2)[CH:27]=[CH:26]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27598671-Methyl-1H-indole-5-boronic acidHCID 58532385HCID 58532385, compound

Product 1

HCID 58532461HCID 58532461, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

6-bromo-1-phenoxy-1H-pyrrolo[3,2-b]pyridine (56 mg, 0.205 mmol, 1.0 eq), Pd(PPh3)4 (13 mg), 2.0 M K2CO3 (1.0 ml), DMF (1.2 ml), and (1-methyl-1H-indol-5-yl)boronic acid (1.5 eq, 0.315 mmol) were refluxed under N2 overnight. The crude products were purified with preparation HPLC to give the product in 50%.

Workup

  1. customThe crude products were purified with preparation HPLC
  2. customto give the product in 50%

Sources & evidence

ORD record
ord-4fb74659ee1e43f4b4594ce9c838587d
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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