Tributylvinyltin → HCID 69099575、化合物

HRID 2251527ノート

反応式

HRID 2251527 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[CH2:9][CH2:10][C:11]2[CH:25]=[CH:24][C:14]([O:15][C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=2)=[N:6][CH:7]=1.[CH:37]([Sn](CCCC)(CCCC)CCCC)=[CH2:38].[Cl-].[Li+].[F-].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.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(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>[CH3:22][C:16]([O:15][C:14]1[CH:24]=[CH:25][C:11]([CH2:10][CH2:9][N:8]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[C:5]2[CH:4]=[CH:3][C:2]([CH:37]=[CH2:38])=[CH:7][N:6]=2)=[CH:12][CH:13]=1)([CH3:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18]

参加物

10

反応物 4

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 59643333HCID 59643333、化合物

生成物 1

HCID 69099575HCID 69099575、化合物収率 52%

試薬・触媒・溶媒 5

HCID 314042,6-Di-tert-butyl-4-methylphenol触媒HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of ethyl 2-[4-(2-{(5-bromopyridin-2-yl)[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (150 mg; 0.27 mmol) in 2 ml of toluene was treated under nitrogen with tetrakis(triphenylphosphine)palladium (0) (61 mg; 0.053 mmol), vinyltributyltin (252 mg; 0.80 mmol), lithium chloride (34 mg; 0.80 mmol) and 2,6-di-tert-butyl-4-methyl-phenol (3 mg). The mixture was heated at 110C overnight. Upon cooling, the mixture was diluted with 10 ml each of ethyl acetate and water. A saturated solution of KF (10 ml) was added and the phases were separated. The organic phase was washed with brine, dried over sodium sulfate and concentrated. Purification by radial chromatography using an ethyl acetate-hexane gradient (5–50%) afforded ethyl 2-methyl-2-(4-{2-[[4-(trifluoromethyl)benzyl](5-vinylpyridin-2-yl)amino]ethyl}phenoxy)propanoate (71 mg; 52% yield).

後処理

  1. temperatureUpon cooling
  2. customthe phases were separated
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification by radial chromatography

出典と根拠

ORDレコード
ord-166a4e085fd94cf3b86f361809af57f2
出典データセット
uspto-grants-2008_01
特許番号
US07319104B2

反応ノート

読み込み中…