Cesium carbonate → Di-tert-butyl {6'-[(3-methoxypyridin-2-yl)amino]dispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl}imidodicarbonate

HRID 594846

反応式

HRID 594846 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:31](=[CH:32][CH:33]=1)[O:30][CH2:29][C:25]1([CH2:28][O:27][CH2:26]1)[C:5]12[CH2:9][O:8][C:7]([N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N:6]1.[CH3:34][O:35][C:36]1[C:37]([NH2:42])=[N:38][CH:39]=[CH:40][CH:41]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:34][O:35][C:36]1[C:37]([NH:42][C:2]2[CH:3]=[C:4]3[C:31](=[CH:32][CH:33]=2)[O:30][CH2:29][C:25]2([CH2:28][O:27][CH2:26]2)[C:5]23[CH2:9][O:8][C:7]([N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N:6]2)=[N:38][CH:39]=[CH:40][CH:41]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 99203842-Amino-3-methoxypyridineHCID 86724239Di-tert-butyl (6'-bromodispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl)imidodicarbonate

生成物 1

HCID 86724238Di-tert-butyl {6'-[(3-methoxypyridin-2-yl)amino]dispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-yl}imidodicarbonate

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of di-tert-butyl (6′-bromodispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl)imidodicarbonate (300 mg, 0.571 mmol), 3-methoxypyridin-2-amine (354 mg, 2.86 mmol), tris(dibenzylideneacetone)dipalladium(0) (105 mg, 0.114 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (198 mg, 0.343 mmol), Cs2CO3 (558 mg, 1.71 mmol) and dioxane (15 mL) was stirred for 48 hours at 100° C. The reaction mixture was cooled down to ambient temperature, and partitioned with CHCl3 and water. The organic layer was dried over Na2SO4, and filtered. The filtrate was concentrated at reduced pressure, to give crude di-tert-butyl {6′-[(3-methoxypyridin-2-yl)amino]dispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl}imidodicarbonate, which was used for the next reaction without further purification.

後処理

  1. temperatureThe reaction mixture was cooled down to ambient temperature
  2. custompartitioned with CHCl3 and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated at reduced pressure

出典と根拠

ORDレコード
ord-553cf72ccbb04e97a70f38172fc4878d
出典データセット
uspto-grants-2016_01
特許番号
US09242973B2

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