Methanesulfonic Acid → 7-bromo-8-fluoro-3-(3-methoxy-3-methylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-2'-amine

HRID 335893ノート

反応式

HRID 335893 の反応式
[NH2:1][C:2]1[O:3][CH2:4][C:5]2([C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]#[C:21][C:22]([CH3:25])([OH:24])[CH3:23])[CH:18]=3)[O:13][C:12]3[C:7]2=[CH:8][C:9]([Br:27])=[C:10]([F:26])[CH:11]=3)[N:6]=1.[CH3:28]S(O)(=O)=O.C([O-])(O)=O.[Na+]>CO>[Br:27][C:9]1[CH:8]=[C:7]2[C:5]3([CH2:4][O:3][C:2]([NH2:1])=[N:6]3)[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]#[C:21][C:22]([O:24][CH3:28])([CH3:23])[CH3:25])[CH:18]=3)[O:13][C:12]2=[CH:11][C:10]=1[F:26]

参加物

5

反応物 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 673829024-(2'-amino-7-bromo-8-fluoro-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazole]-3-yl)-2-methylbut-3-yn-2-ol

生成物 1

HCID 673873667-bromo-8-fluoro-3-(3-methoxy-3-methylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazol]-2'-amine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 4-(2′-amino-7-bromo-8-fluoro-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-3-yl)-2-methylbut-3-yn-2-ol (0.580 g, 1.342 mmol) in 10 mL MeOH was treated with methanesulfonic acid (0.871 mL, 13.42 mmol). The resulting solution was allowed to stir at RT for 72 hours and was then heated at 85° C. for 3 hours. The reaction mixture was poured into saturated NaHCO3 (50 mL) and was extracted with EtOAc (3×25 mL). The organics were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the crude residue by column chromatgraphy [0-100% (95:5 EtOAc/MeOH)/CH2Cl2] afforded 7-bromo-8-fluoro-3-(3-methoxy-3-methylbut-1-ynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine

後処理

  1. temperaturewas then heated at 85° C. for 3 hours
  2. extractionwas extracted with EtOAc (3×25 mL)
  3. washThe organics were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude residue by column chromatgraphy [0-100% (95:5 EtOAc/MeOH)/CH2Cl2]

出典と根拠

ORDレコード
ord-1cf39d7711c4452eafa8b92bf93d7518
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…