2,4-Dimethoxybenzylamine → (7-Bromo-quinolin-2-ylmethyl)-(2,4-dimethoxy-benzyl)-amine

HRID 2176222노트

반응식

HRID 2176222 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=O)=[N:9]2)=[CH:4][CH:3]=1.[CH3:14][O:15][C:16]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:17]=1[CH2:18][NH2:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][NH:19][CH2:18][C:17]3[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:16]=3[O:15][CH3:14])=[N:9]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 5972502,4-DimethoxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 366880237-Bromo-2-quinolinecarboxaldehyde

생성물 1

HCID 86706058(7-Bromo-quinolin-2-ylmethyl)-(2,4-dimethoxy-benzyl)-amine수율 98.3%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

7-Bromo-quinoline-2-carbaldehyde (354 mg, 1.50 mmol, prepared as described in EP 239746) was dissolved in 1,2-dichloroethane (15 mL) and 2,4-dimethoxybenzylamine (251 mg, 225 μL, 1.50 mmol) was added and the reaction mixture stirred for 5 minutes before sodium triacetoxyborohydride (477 mg, 2.25 mmol) was added. After 3.5 h stirring the reaction mixture was quenched with saturated sodium hydrogen carbonate solution and ethyl acetate was added. The organic layer was separated and washed with sodium hydrogen carbonate and the combined aqueous layers were extracted with ethyl acetate. The organic extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered and evaporated to give the crude, title compound as a yellow gum (571 mg) which was used without further purification. LCMS (m/z) 387.0, 389.0 [M+H], Tr=1.57 min.

후처리

  1. additionwas added
  2. customwas quenched with saturated sodium hydrogen carbonate solution and ethyl acetate
  3. additionwas added
  4. customThe organic layer was separated
  5. washwashed with sodium hydrogen carbonate
  6. extractionthe combined aqueous layers were extracted with ethyl acetate
  7. washThe organic extracts were washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customevaporated

출처 및 근거

ORD 기록
ord-03424f6dcdc7400dadfbd1ff3c5df6f6
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062092B2

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