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Ethyl Acetate → HCID 136101881、化合物

HRID 1091734
ノート
印刷プレビュー

反応式

HRID 1091734 の反応式
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]
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

9

反応物 3

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

生成物 1

HCID 136101881HCID 136101881、化合物収率 100%

試薬・触媒・溶媒 5

HCID 142844-(Dimethylamino)pyridine触媒
HCID 98885
Molybdenum carbonyl (Mo(CO)6)
触媒
HCID 178476741HCID 178476741、化合物触媒
HCID 962Water溶媒2 回
HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2ea4038461644a488fb7a6c2de2bd87d
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08129380B2

反応ノート

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