Potassium Carbonate → HCID 86305614, compound

HRID 712597Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([C:12]([NH2:14])=[O:13])[CH2:7][CH2:6][CH2:5]2.[CH3:15][O:16][C:17]1[CH:18]=[N:19][CH:20]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:22]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[CH3:15][O:16][C:17]1[CH:22]=[C:21]([C:2]2[CH:3]=[C:4]3[C:9](=[N:10][CH:11]=2)[N:8]([C:12]([NH2:14])=[O:13])[CH2:7][CH2:6][CH2:5]3)[CH:20]=[N:19][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

6-Bromo-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide (30 mg, 0.12 mmol), 3-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (43 mg, 0.18 mmol) and K2CO3 (32 mg, 0.23 mmol) are mixed in 1.0 mL of 1,4-dioxane and 0.10 mL of water. Argon gas is bubbled through the mixture for 10 min and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (8.3 mg, 0.01 mmol) is added. The mixture is heated at 100° C. for 2 hrs. Then solvents are removed and EtOAc (20 mL) is added. The mixture is filtered to remove any solid and the filtrate is concentrated to give the crude product. Purification by flash column chromatography affords 12.3 mg of the title product.

Workup

customArgon gas is bubbled through the mixture for 10 min
customThen solvents are removed
additionEtOAc (20 mL) is added
filtrationThe mixture is filtered
customto remove any solid
concentrationthe filtrate is concentrated
customto give the crude product
customPurification by flash column chromatography

Sources & evidence

ORD record: ord-b310f6896a1d4af5a6c3e4b918b33bd0
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181272B2

Reaction notes

Loading…