Water → (S)-tert-butyl (1-(4-amino-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)but-3-en-2-yl)carbamate

HRID 336161ノート

反応式

HRID 336161 の反応式
[NH2:1][C:2]1[C:3]2[C:10](I)=[CH:9][N:8]([CH2:12][C@@H:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:14]=[CH2:15])[C:4]=2[N:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CO[CH2:32][CH2:33]OC.O.C(O[CH2:41][CH3:42])(=O)C>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[NH2:1][C:2]1[C:3]2[C:10]([C:10]3[CH:9]=[N:8][C:4]4[C:32]([CH:33]=3)=[CH:42][CH:41]=[CH:2][CH:3]=4)=[CH:9][N:8]([CH2:12][C@@H:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:14]=[CH2:15])[C:4]=2[N:5]=[CH:6][N:7]=1

参加物

7

反応物 5

HCID 962Water2 回HCID 80711,2-DimethoxyethaneHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 86711293HCID 86711293、化合物

生成物 1

HCID 86711294(S)-tert-butyl (1-(4-amino-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)but-3-en-2-yl)carbamate

試薬・触媒・溶媒 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒

反応条件

温度
100 °C

実験手順

A mixture of (S)-tert-butyl (1-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)but-3-en-2-yl)carbamate (8.26 g) obtained in Step 2,3-quinolineboronic acid (4.99 g), cesium carbonate (12.54 g), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (785.6 mg), DME (66 ml), and water (33 ml) was stirred under a nitrogen atmosphere at 100° C. for 2 hours. After cooling the reaction mixture, water and ethyl acetate were added thereto to separate the organic layer. The aqueous layer was then extracted with ethyl acetate twice. The resulting organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate, ethyl acetate/methanol) to obtain the title compound (8.0 g) as a light-orange solid.

後処理

  1. additionwere added
  2. customto separate the organic layer
  3. extractionThe aqueous layer was then extracted with ethyl acetate twice
  4. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate, ethyl acetate/methanol)

出典と根拠

ORDレコード
ord-e256dd50faa34f708c6c8561af5f2490
出典データセット
uspto-grants-2014_11
特許番号
US08889666B2

反応ノート

読み込み中…