Ammonium formate → 4-((4-Fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-ol

HRID 916401노트

반응식

HRID 916401 반응식
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[C:21]([F:30])=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][C:24]([CH3:29])=[CH:23]4)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:31][CH3:32])C1C=CC=CC=1.C([O-])=O.[NH4+]>CN(C=O)C.[Pd].C(OCC)(=O)C>[F:30][C:21]1[C:20]([O:19][C:13]2[C:12]3[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:31][CH3:32])[CH:11]=3)[N:16]=[CH:15][N:14]=2)=[CH:28][CH:27]=[C:26]2[C:22]=1[CH:23]=[C:24]([CH3:29])[NH:25]2

참가 물질

6

반응물 2

HCID 2723923Ammonium formateHCID 101512047-(Benzyloxy)-4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazoline

생성물 1

HCID 1355308324-((4-Fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-ol수율 100%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A suspension of 7-benzyloxy-4-(4-fluoro-2-methylindol-5-yloxy)-6-methoxyquinazoline (8.2 g, 19.1 mmol), ammonium formate (12 g, 190 mmol) in DMF (50 ml) containing 10% palladium on carbon (2 g) was stirred at ambient temperature for 1.5 hours. The mixture was diluted with ethyl acetate and filtered over diatomaceous earth A solid precipitated out of the filtrate. The solid was filtered off. The filtrate was washed with aqueous sodium hydrogen carbonate, followed by brine and dried over magnesium sulphate. The volatiles were removed under vacuum. The residual solid was combined with the solid previously isolated from the filtrate and was then triturated with acetonitrile under cooling. The precipitate was filtered, washed with acetonitrile followed by diethyl ether and dried under vacuum to give 4-(4-fluoro-2-methylindol-5-yloxy)-7-hydroxy-6-methoxyquinazoline (6.48 g, quant.).

후처리

  1. filtrationfiltered over diatomaceous earth A solid
  2. customprecipitated out of the filtrate
  3. filtrationThe solid was filtered off
  4. washThe filtrate was washed with aqueous sodium hydrogen carbonate
  5. dry with materialdried over magnesium sulphate
  6. customThe volatiles were removed under vacuum
  7. custompreviously isolated from the filtrate
  8. customwas then triturated with acetonitrile
  9. temperatureunder cooling
  10. filtrationThe precipitate was filtered
  11. washwashed with acetonitrile
  12. customdried under vacuum

출처 및 근거

ORD 기록
ord-289456bb6a3f4541a75a458c7bda6fe1
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268230B2

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