Triphenylphosphine → 3-{5-[4-(4-Bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl]-tetrazol-1-yl}-propionitrile

HRID 15923

反応式

HRID 15923 の反応式
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:20]([CH2:22][CH2:23][NH:24][C:25]([C:27]1[C:32]([NH:33][C:34]2[CH:39]=[CH:38][C:37]([Br:40])=[CH:36][C:35]=2[F:41])=[C:31]([CH3:42])[C:30](=[O:43])[N:29]([CH3:44])[CH:28]=1)=O)#[N:21].CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Si]([N:63]=[N+:64]=[N-:65])(C)(C)C>CC#N.C(OCC)(=O)C>[Br:40][C:37]1[CH:38]=[CH:39][C:34]([NH:33][C:32]2[C:27]([C:25]3[N:24]([CH2:23][CH2:22][C:20]#[N:21])[N:65]=[N:64][N:63]=3)=[CH:28][N:29]([CH3:44])[C:30](=[O:43])[C:31]=2[CH3:42])=[C:35]([F:41])[CH:36]=1

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 5363146Diisopropyl azodicarboxylateHCID 666743774-(4-Bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (2-cyano-ethyl)-amide

生成物 1

HCID 666744343-{5-[4-(4-Bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydro-pyridin-3-yl]-tetrazol-1-yl}-propionitrile収率 61%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

PPh3 (83 mg, 0.32 mmol) was added to a stirred suspension of 4-(4-bromo-2-fluorophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (2-cyano-ethyl)-amide (51 mg, 0.12 mmol) in MeCN (1.5 mL). DIAD (0.065 mL, 0.31 mmol) and TMSN3 (0.045 mL, 0.32) were added dropwise. After 22 hours, the reaction mixture was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography gave clean desired product (33 mg, 61%).

後処理

  1. washwashed with water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography

出典と根拠

ORDレコード
ord-0b8af127f4334c3294b8f6645ddf672d
出典データセット
uspto-grants-2010_06
特許番号
US07732616B2

関連ノート

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