Sodium hydride → methyl 5-bromo-4-(2-tert-butoxy-2-oxoethyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 1008969

반응식

HRID 1008969 반응식
[Br:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[S:9][C:4]=2[C:3]=1[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[H-].[Na+].Br[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>CN(C=O)C.CCOC(C)=O.Cl>[Br:1][C:2]1[N:6]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:5]2[CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[S:9][C:4]=2[C:3]=1[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 58679077methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

생성물 1

HCID 67298685methyl 5-bromo-4-(2-tert-butoxy-2-oxoethyl)-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate수율 80%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution (0.2 M) of methyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate (from Step 1) in dry DMF was treated with sodium hydride (2 eq., 60% suspension in mineral oil) at 0° C. The reaction mixture was stirred at RT for 30 min then tert-butyl bromoacetate (3 eq.) was added. The reaction was heated to 50° C. for 1 h. After cooling, the solution was diluted with EtOAc and 1 N hydrochloric acid was added. The organic phase was washed with 1 N hydrochloric acid, saturated NaHCO3 solution and brine, dried over sodium sulfate and evaporated in vacuo to give a residue that was purified by flash chromatography (PE:EtOAc, 9:1) to afford the title compound (80%) as a solid. 1H-NMR (400 MHz, DMSO-d6, 300 K, δ) 7.99 (s, 1H), 4.99 (s, 2H), 3.82 (s, 3H), 2.66-2.52 (m, 1H), 1.82-1.21 (m, 101H), 1.42 (s, 9H). MS (ES+) m/z: 456, 458 [M+H]+.

후처리

  1. temperatureThe reaction was heated to 50° C. for 1 h
  2. temperatureAfter cooling
  3. additionwas added
  4. washThe organic phase was washed with 1 N hydrochloric acid, saturated NaHCO3 solution and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customto give a residue that
  8. customwas purified by flash chromatography (PE:EtOAc, 9:1)

출처 및 근거

ORD 기록
ord-c92a4a79b5eb4615a6f250f550b4246b
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973026B2

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