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 335742노트

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HRID 335742 반응식
[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

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6a50463b5ca543ecaaec1fcada88b4bb
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883782B2

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