Potassium Carbonate → (S)-5-(2'-amino-3-(3,3-dimethylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazole]-7-yl)nicotinonitrile

HRID 335742ノート

反応式

HRID 335742 の反応式
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[N:7][CH:8]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[C:24]1[CH:25]=[C:26]2[C@@:37]3([CH2:41][O:40][C:39]([NH2:42])=[N:38]3)[C:36]3[C:31](=[N:32][CH:33]=[C:34]([C:43]#[C:44][C:45]([CH3:48])([CH3:47])[CH3:46])[CH:35]=3)[O:30][C:27]2=[CH:28][CH:29]=1)(=O)=O.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>[NH2:42][C:39]1[O:40][CH2:41][C@:37]2([C:36]3[C:31](=[N:32][CH:33]=[C:34]([C:43]#[C:44][C:45]([CH3:46])([CH3:47])[CH3:48])[CH:35]=3)[O:30][C:27]3[C:26]2=[CH:25][C:24]([C:5]2[CH:6]=[N:7][CH:8]=[C:3]([CH:4]=2)[C:1]#[N:2])=[CH:29][CH:28]=3)[N:38]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 450795765-Cyanopyridine-3-boronic acidHCID 86640725(S)-2'-amino-3-(3,3-dimethylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazole]-7-yl trifluoromethanesulfonate

生成物 1

HCID 58466178(S)-5-(2'-amino-3-(3,3-dimethylbut-1-ynyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-oxazole]-7-yl)nicotinonitrile

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-cyanopyridin-3-ylboronic acid (0.030 g, 0.206 mmol), palladiumtetrakis (10.80 mg, 9.35 μmol), potassium carbonate (0.129 g, 0.935 mmol), and (S)-2′-amino-3-(3,3-dimethylbut-1-ynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-7-yl trifluoromethanesulfonate (0.090 g, 0.187 mmol) was treated with 1 mL of dioxane followed by 0.4 mL water. The vial was flushed with argon and was heated to 80° C. for 4 hours. The reaction mixture was diluted with EtOAc and dried over MgSO4. The organics were then concentrated, and the crude residue was purified by column chromatography yielding (S)-5-(2′-amino-3-(3,3-dimethylbut-1-ynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazole]-7-yl)nicotinonitrile.

後処理

  1. customThe vial was flushed with argon
  2. additionThe reaction mixture was diluted with EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationThe organics were then concentrated
  5. customthe crude residue was purified by column chromatography

出典と根拠

ORDレコード
ord-6a50463b5ca543ecaaec1fcada88b4bb
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…