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Tetrahydrofuran → HCID 136348435、化合物

HRID 1748767
ノート
印刷プレビュー

反応式

HRID 1748767 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

HCID 136348435HCID 136348435、化合物収率 64%

試薬・触媒・溶媒 2

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

反応条件

温度
120 °C

実験手順

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)+

後処理

  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)

出典と根拠

ORDレコード
ord-6e305a7633324b9498db47a11b618321
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09150592B2

反応ノート

読み込み中…

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