Potassium Carbonate → 1-(2'-amino-7-(5-chloro-2-fluorophenyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazole]-3-yloxy)propan-2-one

HRID 335814ノート

反応式

HRID 335814 の反応式
[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

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 3718925(5-Chloro-2-fluoro-phenyl)boronic acidHCID 673830821-(2'-amino-7-bromo-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazole]-3-yloxy)propan-2-one

生成物 1

HCID 673830551-(2'-amino-7-(5-chloro-2-fluorophenyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazole]-3-yloxy)propan-2-one

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

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].

後処理

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

出典と根拠

ORDレコード
ord-90a9f01216e04a9c85c54a0825cb7e88
出典データセット
uspto-grants-2014_11
特許番号
US08883782B2

反応ノート

読み込み中…