Dimethylformamide → HCID 85997603, 화합물

HRID 2252238노트

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HRID 2252238 반응식
Br[C:2]1[CH:3]=[C:4]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[C:7]1[NH:8][N:9]=[CH:10][C:6]=1[CH2:5]2.[Li]C1C=CC=CC=1.[Li]C(CC)C.CN([CH:31]=[O:32])C>C1COCC1>[CH3:15][O:14][C:13]1[CH:12]=[C:11]2[C:4]([CH2:5][C:6]3[CH:10]=[N:9][NH:8][C:7]=32)=[CH:3][C:2]=1[CH:31]=[O:32]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 69201862HCID 69201862, 화합물HCID 178418400CID 53628100HCID 178506676HCID 178506676, 화합물

생성물 1

HCID 85997603HCID 85997603, 화합물수율 81.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

To a suspension of Example 104C (5.49 g, 0.0207 mol) in THF (300 mL) was added PhLi (1.9 M, 21.8 mL, 0.0414 mol) at −78° C. s-BuLi (1.4 M, 29.6 mL, 0.0414 mol) and DMF (12.8 mL, 0.166 mol) were added to the reaction mixture after 30 and 60 minutes, respectively. The mixture was stirred at −78° C. for 1 hour and the cold bath was removed. The reaction was quenched with saturated NH4Cl solution after 1 hour at room temperature. The mixture was extracted with EtOAc, washed with water, brine, dried over MgSO4, filtered, concentrated, and triturated with ether to give 3.62 g (81%) of the desired product. MS (DCI/NH3) m/z: 215.1 (M+H)+; 1H NMR (300 MHz, DMSO-D6) δ ppm 3.62 (s, 2H) 4.01 (s, 3H) 7.45 (s, 1H), 7.73 (s, 1H) 7.80 (s, 1H) 10.37 (s, 1H) 13.07 (s, 1H).

후처리

  1. additionwere added to the reaction mixture after 30 and 60 minutes
  2. customthe cold bath was removed
  3. customThe reaction was quenched with saturated NH4Cl solution after 1 hour at room temperature
  4. extractionThe mixture was extracted with EtOAc
  5. washwashed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customtriturated with ether

출처 및 근거

ORD 기록
ord-fac2390ff7704c32ba1d519c2f63ad60
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07320986B2

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