Potassium Carbonate → HCID 66781392, compound

HRID 1095745Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9](B(O)O)[CH:8]=1.Br[C:17]1[CH:22]=[CH:21][N:20]2[CH:23]=[CH:24][N:25]=[C:19]2[CH:18]=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.O>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:17]2[CH:22]=[CH:21][N:20]3[CH:23]=[CH:24][N:25]=[C:19]3[CH:18]=2)[CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of potassium carbonate (0.351 g, 2.54 mmol), pyridin-3-ylboronic acid (68.6 mg, 0.558 mmol), 7-bromoimidazo[1,2-a]pyridine (0.100 g, 0.508 mmol) and tetrakis(triphenylphosphine)palladium (0) (29.3 mg, 0.025 mmol) in 6.5 ml of a 1:1:4.5 mixture of water:dimethylformamide:acetonitrile was degassed thoroughly under a nitrogen atmosphere, and heated at 60° C. for 18 hours. The reaction mixture was poured in water (50 ml) and extracted with dichloromethane and EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated to afford a solid. The solid was purified by silica gel chromatography (eluting with 6% MeOH-chloroform) to afford the desired compound (74.1 mg, 75% yield). MS APCI (+) m/z 196.3 (M+1) detected.

Workup

customdimethylformamide:acetonitrile was degassed thoroughly under a nitrogen atmosphere
additionThe reaction mixture was poured in water (50 ml)
extractionextracted with dichloromethane and EtOAc
dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
concentrationconcentrated
customto afford a solid
customThe solid was purified by silica gel chromatography (eluting with 6% MeOH-chloroform)

Sources & evidence

ORD record: ord-0fb4fa8ab0d447e8b13ccc5b7911b951
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138181B2

Reaction notes

Loading…