Cesium carbonate → HCID 60042063、化合物

HRID 449998ノート

反応式

HRID 449998 の反応式
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([NH:9][C:10]([C:12]1[C:16]3[CH:17]=[CH:18][C:19](Br)=[CH:20][C:15]=3S[N:13]=1)=[O:11])[CH2:2]2.C[C:23]1(C)[C:36]2[CH:35]=[CH:34][CH:33]=[C:32](P(C3C=CC=CC=3)C3C=CC=CC=3)[C:31]=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.[C:64](=[O:67])([O-])[O-].[Cs+].[Cs+].[C:70](=[NH:83])([C:77]1[CH:82]=[CH:81]C=CC=1)C1C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([NH:9][C:10]([C:12]1[C:16]3[C:15](=[CH:20][CH:19]=[C:18]([N:1]4[CH2:2][CH2:3][CH:64]([O:67][CH2:23][C:36]5[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH2:6]4)[CH:17]=3)[N:83]([CH2:70][CH:77]3[CH2:82][CH2:81]3)[N:13]=1)=[O:11])[CH2:2]2

参加物

6

反応物 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 10044409HCID 10044409、化合物

生成物 1

HCID 60042063HCID 60042063、化合物収率 79%

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

実験手順

The mixture of N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromo-1,2-benzisothiazole-3-carboxamide (6.30 mmol), palladium acetate (1.00 mmol), and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (Xantphos) (0.700 mmol) was evacuated and back-fill with Ar gas. The solids were diluted with tetrahydrofuran (150 mL) and treated with cesium carbonate (7.00 mmol) and benzophenone imine (6.80 mmol). The reaction mixture was heated at reflux for 16 h. The reaction mixture was concentrated and redissolved in a mixture of tetrahydrofuran (90 mL) and 3 N hydrochloric acid (30 mL). The reaction mixture was maintained for 2 h and was concentrated. The residue was purified by chromatography using a mixture of 70/30/1 ethyl acetate/methanol/ammonium hydroxide, thus providing the aniline in 79% yield. The aniline was used directly in subsequent reactions.

後処理

  1. customwas evacuated and back-fill with Ar gas
  2. additionThe solids were diluted with tetrahydrofuran (150 mL)
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 16 h
  5. concentrationThe reaction mixture was concentrated
  6. dissolutionredissolved in a mixture of tetrahydrofuran (90 mL) and 3 N hydrochloric acid (30 mL)
  7. temperatureThe reaction mixture was maintained for 2 h
  8. concentrationwas concentrated
  9. customThe residue was purified by chromatography
  10. additiona mixture of 70/30/1 ethyl acetate/methanol/ammonium hydroxide

出典と根拠

ORDレコード
ord-07d600471cba4f7ca4fba64ed06ed26d
出典データセット
uspto-grants-2013_07
特許番号
US08486937B2

反応ノート

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