Potassium Carbonate → HCID 67383055, compound

HRID 335814Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6](B(O)O)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:18][C:19]1[O:20][CH2:21][C:22]2([C:36]3[C:31](=[N:32][CH:33]=[C:34]([O:37][CH2:38][C:39](=[O:41])[CH3:40])[CH:35]=3)[O:30][C:29]3[C:24]2=[CH:25][C:26](Br)=[CH:27][CH:28]=3)[N:23]=1.O1CCOCC1>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>[NH2:18][C:19]1[O:20][CH2:21][C:22]2([C:36]3[C:31](=[N:32][CH:33]=[C:34]([O:37][CH2:38][C:39](=[O:41])[CH3:40])[CH:35]=3)[O:30][C:29]3[C:24]2=[CH:25][C:26]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[F:11])=[CH:27][CH:28]=3)[N:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A vial charged with 5-chloro-2-fluorophenylboronic acid (0.431 g, 2.474 mmol), palladiumtetrakis (0.057 g, 0.049 mmol), potassium carbonate (0.684 g, 4.95 mmol), and 1-(2′-amino-7-bromo-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-3-yloxy)propan-2-one (0.400 g, 0.990 mmol) was treated with 5 mL dioxane followed by 1 mL water. The vial was flushed with argon and was heated to 80° C. for 3 hours. The reaction mixture was diluted with EtOAc (25 mL) and dried over MgSO4. The organic layers were combined and concentrated, and the crude residue was purified by column chromatography yielding 1-(2′-amino-7-(5-chloro-2-fluorophenyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-3-yloxy)propan-2-one. MS m/z=454.0 [M+H].

Workup

customThe vial was flushed with argon
additionThe reaction mixture was diluted with EtOAc (25 mL)
dry with materialdried over MgSO4
concentrationconcentrated
customthe crude residue was purified by column chromatography

Sources & evidence

ORD record: ord-90a9f01216e04a9c85c54a0825cb7e88
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883782B2

Reaction notes

Loading…