Trifluoroacetic acid → [5-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-yl]-(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-amine

HRID 510010노트

반응식

HRID 510010 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:12]3[CH:13]=[CH:14][C:15]([NH2:19])=[N:16][C:17]=3[F:18])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[F:20][C:21]1[CH:22]=[C:23]([CH:29]=O)[C:24]([O:27][CH3:28])=[N:25][CH:26]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:12]3[CH:13]=[CH:14][C:15]([NH:19][CH2:29][C:23]4[C:24]([O:27][CH3:28])=[N:25][CH:26]=[C:21]([F:20])[CH:22]=4)=[N:16][C:17]=3[F:18])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

참가 물질

5

반응물 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 226783235-Fluoro-2-methoxynicotinaldehydeHCID 582594945-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-ylamine

생성물 1

HCID 58259257[5-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-yl]-(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-amine

반응 조건

온도
80 °C

실험 절차

To 5-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-6-fluoro-pyridin-2-ylamine (173, 1 equivalent) and 5-fluoro-2-methoxy-pyridine-3-carbaldehyde (37, 1 equivalent), triethylsilane (4 equivalents) and trifluoroacetic acid (4 equivalents) are added. The reaction is stirred at 80° C. for several hours, then concentrated under vacuum. The resulting material is taken up in ethyl acetate and extracted with addition of aqueous potassium carbonate. The organic layer is concentrated under vacuum, then triturated with dichloromethane to provide the desired compound.

후처리

  1. concentrationconcentrated under vacuum
  2. extractionextracted with addition of aqueous potassium carbonate
  3. concentrationThe organic layer is concentrated under vacuum
  4. customtriturated with dichloromethane

출처 및 근거

ORD 기록
ord-71267a7496684dc89201e00a2ee02d12
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096593B2

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