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Sodium Bicarbonate → 5-(2-(2'-(Trifluoromethyl)biphenyl-4-yl)ethyl)indoline

HRID 710446
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인쇄 미리보기

반응식

HRID 710446 반응식
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][CH:21]=[CH:20]3)=[CH:11][CH:10]=1.[BH3-]C#N.[Na+].C([O-])(O)=O.[Na+]>CC(O)=O>[F:27][C:2]([F:1])([F:26])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][CH2:21][CH2:20]3)=[CH:13][CH:14]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 667266155-(2-(2'-(Trifluoromethyl)biphenyl-4-yl)ethyl)-1H-indole

생성물 1

HCID 667262965-(2-(2'-(Trifluoromethyl)biphenyl-4-yl)ethyl)indoline수율 75.4%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

The product of Step C (0.24 g, 0.65 mmol) was dissolved in AcOH (2 ml) and NaCNBH3 (0.082 g, 1.3 mmol) was added in portions. The mixture was stirred for 1 h and then poured into an aqueous solution of NaHCO3 and extracted with EtOAc (50 ml). The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2) to give the desired product (0.18 g, 75%), as pale paste. 1H-NMR (CDCl3) 2.81-2.94 (m, 4H); 3.0 (tr, 2H, J=7.22 Hz); 3.54 (tr, 2H, J=8.35 Hz); 6.58 (d, 1H, J=7.83 Hz); 6.84 (d, 1H, J=7.82 Hz); 6.9 (b, 1H); 7.17-7.21 (m, 3H); 7.31-7.35 (m, 2H); 7.43 (tr, 1H, J=7.65 Hz); 7.54 (tr, 1H, J=7.37 Hz); 7.72 (d, 1H, J=7.78 Hz).

후처리

  1. extractionextracted with EtOAc (50 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by FCC (SiO2)

출처 및 근거

ORD 기록
ord-26a27f8ff9a04bf9b8152cd8adeee215
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09181182B2

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