5-Bromonicotinamide → 5-{1'-tert-Butoxycarbonyl-4-oxospiro[chroman-2,4'-piperidin]-6-yl}nicotinamide

HRID 38474

反応式

HRID 38474 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].Br[C:34]1[CH:35]=[N:36][CH:37]=[C:38]([CH:42]=1)[C:39]([NH2:41])=[O:40].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:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([CH2:22][C:21](=[O:23])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:34]4[CH:35]=[N:36][CH:37]=[C:38]([CH:42]=4)[C:39]([NH2:41])=[O:40])[CH:19]=3)[O:14]2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

8

反応物 3

HCID 18085-BromonicotinamideHCID 10340Sodium CarbonateHCID 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 579310025-{1'-tert-Butoxycarbonyl-4-oxospiro[chroman-2,4'-piperidin]-6-yl}nicotinamide

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 (1.43 g, 3.23 mmol), 5-bromonicotinamide (778 mg, 3.87 mmol), Pd(PPh3)4 (372 mg, 0.322 mmol), and aqueous 2M Na2CO3 (10 ml) solution were suspended in dioxane (20 ml) and heated at 100° C. for 4 h. The reaction mixture was diluted with CHCl3 and H2O, the aqueous layer was extracted with CHCl3. The combined organic layer was dried over MgSO4. The desiccant was removed through celite filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified through silica gel column chromatography (EtOAc/Acetone) to obtain the intended compound as a pale yellow foam.

後処理

  1. extractionthe aqueous layer was extracted with CHCl3
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. customThe desiccant was removed through celite filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (EtOAc/Acetone)

出典と根拠

ORDレコード
ord-7e06f045e1ef42b1b489e3e145c87c11
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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