Dimethylformamide → HCID 85997603、化合物

HRID 2252238ノート

反応式

HRID 2252238 の反応式
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]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 69201862HCID 69201862、化合物HCID 178418400CID 53628100HCID 178506676HCID 178506676、化合物

生成物 1

HCID 85997603HCID 85997603、化合物収率 81.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fac2390ff7704c32ba1d519c2f63ad60
出典データセット
uspto-grants-2008_01
特許番号
US07320986B2

反応ノート

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