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Ethyl Acetate → HCID 136101881, 화합물

HRID 1091734
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HRID 1091734 반응식
Br[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][C:6]1[C:7]2[C:8](=[C:13]([CH3:17])[NH:14][C:15]=2[CH3:16])[C:9](=[O:12])[NH:10][N:11]=1.C(N(C(C)C)C(C)C)C.CC[O:32][C:33](C)=[O:34]>CN(C)C1C=CN=CC=1.O1CCOCC1.O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].C(O[Pd]CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C)(=O)C>[CH3:16][C:15]1[NH:14][C:13]([CH3:17])=[C:8]2[C:7]=1[C:6]([CH2:5][C:4]1[CH:3]=[C:2]([CH:20]=[CH:19][CH:18]=1)[C:33]([OH:34])=[O:32])=[N:11][NH:10][C:9]2=[O:12]
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참가 물질

9

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HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 1361018774-(3-bromobenzyl)-5,7-dimethyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-one

생성물 1

HCID 136101881HCID 136101881, 화합물수율 100%

시약·촉매·용매 5

HCID 142844-(Dimethylamino)pyridine촉매
HCID 98885
Molybdenum carbonyl (Mo(CO)6)
촉매
HCID 178476741HCID 178476741, 화합물촉매
HCID 962Water용매2회
HCID 312751,4-Dioxane용매

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온도
150 °C

실험 절차

4-(3-Bromobenzyl)-5,7-dimethyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-one (50) (0.188 g, 0.57 mmol), molybdenum hexacarbonyl (0.224 g, 0.85 mmol), N,N-dimethylpyridin-4-amine (0.138 g, 1.13 mmol), N-ethyl-N-isopropylpropan-2-amine (0.197 mL, 1.13 mmol) and acetoxy(2-(dio-tolylphosphino)benzyl)palladium (0.027 g, 0.03 mmol) were suspended in a mixture of dioxane (2.0 mL) and water (2.0 mL) and sealed into a microwave tube. The reaction was heated to 150° C. for 30 minutes in the microwave reactor and cooled to room temperature. The reaction mixture was diluted with water (50 mL) and EtOAc (50 mL). The mixture was filtered through celite. The layers were separated and the aqueous was adjusted to pH2 with 2M HCl. The resulting precipitate was collected by filtration, washed with water (50 mL), Et2O (50 mL) and dried under vacuum to afford the desired material as a brown solid (0.200 g, >100% yield), which was used without further purification. 1H NMR (400.132 MHz, DMSO) δ 2.26 (3H, s), 2.51 (3H, s), 4.13 (2H, s), 7.39-7.48 (2H, m), 7.78 (2H, m), 11.08 (1H, s), 11.93 (1H, s), 12.86 (1H, s); m/z (LC-MS, ESI+), RT=1.41 min (M+H=298.08).

후처리

  1. customsealed into a microwave tube
  2. temperaturecooled to room temperature
  3. filtrationThe mixture was filtered through celite
  4. customThe layers were separated
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water (50 mL), Et2O (50 mL)
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-2ea4038461644a488fb7a6c2de2bd87d
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08129380B2

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