Cesium carbonate → HCID 60042063, 화합물

HRID 2383396노트

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HRID 2383396 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 60042063HCID 60042063, 화합물수율 79%

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-73e295f7ad8f469eba95bcdb0b9235db
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263619B2

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