Cesium carbonate → HCID 86704416、化合物

HRID 1748223ノート

反応式

HRID 1748223 の反応式
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.[CH:16]12[NH:23][CH:20]([CH2:21][CH2:22]1)[CH2:19][CH:18]([O:24][CH2:25][C:26]1[C:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[O:40][C:41]([F:44])([F:43])[F:42])=[N:28][O:29][C:30]=1[CH:31]1[CH2:33][CH2:32]1)[CH2:17]2.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH:31]1([C:30]2[O:29][N:28]=[C:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[O:40][C:41]([F:42])([F:43])[F:44])[C:26]=2[CH2:25][O:24][CH:18]2[CH2:17][CH:16]3[N:23]([C:2]4[CH:7]=[CH:6][N:5]5[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][N:10]=[C:4]5[CH:3]=4)[CH:20]([CH2:21][CH2:22]3)[CH2:19]2)[CH2:32][CH2:33]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 67260906Ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylateHCID 67983256HCID 67983256、化合物

生成物 1

HCID 86704416HCID 86704416、化合物

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
120 °C

実験手順

A sealable vessel was charged with ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate (67 mg, 0.25 mmol), 4-((8-azabicyclo[3.2.1]octan-3-yloxy)methyl)-5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazole (I-1H) cesium carbonate (122 mg, 0.38 mmol), 1,4-dioxane (2 mL). The mixture was degassed (argon bubble, 10 min) and then tris(dibenzylideneacetone)dipalladium(0) (11 mg, 0.012 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (14 mg, 0.025 mmol) were added. The reaction flask was evacuated and backfilled with Ar three successive times, and then heated to 120° C. for 12 hours. The reaction mixture was cooled to RT, diluted with ethyl acetate (8 mL) and filtered through a CELITE® pad, the filtrate was washed with water (7 mL), dried over magnesium sulfate, concentrated, and chromatographed on silica using linear gradient, 0-100%, EtOAc in Hexanes) to give the desired product as a waxy solid.

後処理

  1. customThe mixture was degassed
  2. custom(argon bubble, 10 min)
  3. customThe reaction flask was evacuated
  4. temperatureThe reaction mixture was cooled to RT
  5. additiondiluted with ethyl acetate (8 mL)
  6. filtrationfiltered through a CELITE® pad
  7. washthe filtrate was washed with water (7 mL)
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customchromatographed on silica using linear gradient, 0-100%, EtOAc in Hexanes)

出典と根拠

ORDレコード
ord-2fdc9b0b3ab0485db865304d8a101b2d
出典データセット
uspto-grants-2015_10
特許番号
US09150568B2

反応ノート

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