HCID 10702137, 화합물 → HCID 10286804, 화합물

HRID 2105583노트

반응식

HRID 2105583 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][OH:12])=[CH:5]2.N[C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)N[C:18]([C:23]([O:25]CC)=O)=[CH:17]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[C:4]([C:22]1[CH:14]=[CH:15][C:16](/[CH:17]=[CH:18]/[C:23]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6]([CH2:11][OH:12])=[CH:5]3)=[O:25])=[CH:20][CH:21]=1)([CH3:8])([CH3:5])[CH3:3]

참가 물질

4

반응물 3

HCID 10702137HCID 10702137, 화합물HCID 10726872Ethyl 5-amino-1H-indole-2-carboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 10286804HCID 10286804, 화합물

반응 조건

온도
25 °C

실험 절차

(5-Aminoindol-2-yl)methan-1-ol. Ethyl 5-aminoindole-2-carboxylate, Example 74(a), (1.5 g, 7.3 mmol) was transferred to a round-bottomed flask and treated with lithium aluminum hydride (10 mL, 10 mmol, 1.0 M in THF, Aldrich) under N2. The reaction mixture was magnetically stirred at 25° C. for 1 h, then quenched by the dropwise addition of H2O (0.5 mL) followed by 20% aq. KOH (30 mL). The suspension was filtered and the aqueous phase extracted with EtOAc. The organic extract was concentrated in vacuo. Purification of the crude product by silica gel chromatography (20:80 hexane:EtOAc) provided the title product. MS (ESI, pos. ion) m/z: 163 (M+1).

후처리

  1. customquenched by the dropwise addition of H2O (0.5 mL)
  2. filtrationThe suspension was filtered
  3. extractionthe aqueous phase extracted with EtOAc
  4. extractionThe organic extract
  5. concentrationwas concentrated in vacuo
  6. customPurification of the crude product by silica gel chromatography (20:80 hexane:EtOAc)

출처 및 근거

ORD 기록
ord-b80a0b459a424ded96f7965da2ce9ce7
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07579347B2

반응 노트

불러오는 중…