Sodium Carbonate → tert-Butyl 6-(5-carbamoylpyridin-2-yl)-4-oxospiro[chroman-2,4'-piperidine]-1'-carboxylate

HRID 38478

反応式

HRID 38478 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:22][C:21](=[O:23])[C:20]3[C:15](=[CH:16][CH:17]=[C:18](B4OC(C)(C)C(C)(C)O4)[CH:19]=3)[O:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:34]1[CH:42]=[CH:41][C:37]([C:38]([NH2:40])=[O:39])=[CH:36][N:35]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C(Cl)(Cl)Cl.O.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>[C:38]([C:37]1[CH:41]=[CH:42][C:34]([C:18]2[CH:19]=[C:20]3[C:15](=[CH:16][CH:17]=2)[O:14][C:11]2([CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]2)[CH2:22][C:21]3=[O:23])=[N:35][CH:36]=1)(=[O:39])[NH2:40]

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 804566-ChloronicotinamideHCID 579309611'-Tert-butoxycarbonyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[chroman-2,4'-piperidin]-4-one

生成物 1

HCID 58208682tert-Butyl 6-(5-carbamoylpyridin-2-yl)-4-oxospiro[chroman-2,4'-piperidine]-1'-carboxylate

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

1′-tert-butoxycarbonyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[chroman-2,4′-piperidin]-4-one (40.0 g, 90.0 mmol), 6-chloronicotinamide (17.0 g, 108 mmol), Pd(PPh3)4 (5.21 g, 4.51 mmol), and aqueous 2M Na2CO3 (100 ml) solution were suspended in dioxane (300 ml) and heated at 100° C. for 16 h. The reaction mixture was diluted with CHCl3 and H2O, the aqueous layer was extracted with CHCl3. The combined organic layer was washed with brine, dried over MgSO4 and silicagel. The desiccant was removed through celite filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by crystallization (CHCl3-EtOAc) to obtain the intended compound as a colorless solid.

後処理

  1. extractionthe aqueous layer was extracted with CHCl3
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over MgSO4 and silicagel
  4. customThe desiccant was removed through celite filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by crystallization (CHCl3-EtOAc)

出典と根拠

ORDレコード
ord-71529f5fb4fa4deb990dc0de44b47136
出典データセット
uspto-grants-2013_09
特許番号
US08524730B2

関連ノート

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