Tetrahydrofuran → HCID 136348435, 화합물

HRID 1748767노트

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HRID 1748767 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[S:14][C:13]([CH3:16])([CH3:15])[CH2:12][NH:11][C:10]3[N:17]([CH3:21])[N:18]=[C:19]([CH3:20])[C:9]2=3)=[C:4]([CH3:22])[CH:3]=1.N12CCCN=C1CCCCC2.[NH2:34][C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1.C1C[O:44][CH2:43]C1>CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[CH3:22][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[CH:8]1[S:14][C:13]([CH3:16])([CH3:15])[CH2:12][NH:11][C:10]2[N:17]([CH3:21])[N:18]=[C:19]([CH3:20])[C:9]1=2)[C:43]([NH:34][C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1)=[O:44]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 100093-AminopyridineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 136216142HCID 136216142, 화합물

생성물 1

HCID 136348435HCID 136348435, 화합물수율 64%

시약·촉매·용매 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)촉매HCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)촉매

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온도
120 °C

실험 절차

To THF (5 mL) was added 4-(4-bromo-2-methyl-phenyl)-1,3,6,6-tetramethyl-7,8-dihydro-4H-pyrazolo[3,4-e][1,4]thiazepine (0.1 g, 0.26 mmol, Example D.58), trans-di-MU-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium(II) (0.025 g, 0.026 mmol, Alfa Aesar), molybdenumhexacarbonyl (0.072 g, 0.26 mmol, Fluka), tri-tert-butylphosphonium tetrafluoroboronate (0.016 g, 0.052 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.061 g, 0.052 mmol) and 3-aminopyridine (0.075 g, 0.78 mmol). The resulting mixture was heated, in a sealed microwave vessel, for about 1 h at about 120° C. in a microwave. After cooling to rt, the mixture was filtered and partitioned between ethyl acetate (50 mL) and 5% aqueous sodium bicarbonate (25 mL). The layers were separated and the organic layer was washed with 5% aqueous sodium bicarbonate (10 mL), dried (MgSO4), filtered and concentrated in vacuo. The resulting oil was purified by column chromatography (SiO2, ethyl acetate followed by 2% MeOH/ethyl acetate to 5% MeOH/ethyl acetate) to afford 3-methyl-N-(3-pyridyl)-4-(1,3,6,6-tetramethyl-7,8-dihydro-4H-pyrazolo[3,4-e][1,4]thiazepin-4-yl)benzamide (0.071 g, 64%) as white solid: LC-MS (Table 1, Method e) Rt=4.87 min, m/z 422 (M+H)+

후처리

  1. temperatureAfter cooling to rt
  2. filtrationthe mixture was filtered
  3. custompartitioned between ethyl acetate (50 mL) and 5% aqueous sodium bicarbonate (25 mL)
  4. customThe layers were separated
  5. washthe organic layer was washed with 5% aqueous sodium bicarbonate (10 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting oil was purified by column chromatography (SiO2, ethyl acetate followed by 2% MeOH/ethyl acetate to 5% MeOH/ethyl acetate)

출처 및 근거

ORD 기록
ord-6e305a7633324b9498db47a11b618321
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150592B2

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