Triphenylphosphine → 6-(3-Bromopropoxy)-4-(4-fluoro-2-methylindol-5-yloxy)-7-methoxyquinazoline

HRID 916410노트

반응식

HRID 916410 반응식
N(C(OCC)=O)=NC(OCC)=O.[F:13][C:14]1[C:22]([O:23][C:24]2[C:33]3[C:28](=[CH:29][C:30]([O:35][CH3:36])=[C:31]([OH:34])[CH:32]=3)[N:27]=[CH:26][N:25]=2)=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[C:17]([CH3:37])[NH:18]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:57][CH2:58][CH2:59][CH2:60]O.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl>[Br:57][CH2:58][CH2:59][CH2:60][O:34][C:31]1[CH:32]=[C:33]2[C:28](=[CH:29][C:30]=1[O:35][CH3:36])[N:27]=[CH:26][N:25]=[C:24]2[O:23][C:22]1[C:14]([F:13])=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([CH3:37])=[CH:16]2

참가 물질

7

반응물 5

HCID 11776Triphenylphosphine2회HCID 123083-Bromo-1-propanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5462977Diethyl azodicarboxylateHCID 112677704-(4-Fluoro-2-methylindol-5-yloxy)-6-hydroxy-7-methoxyquinazoline

생성물 1

HCID 589602506-(3-Bromopropoxy)-4-(4-fluoro-2-methylindol-5-yloxy)-7-methoxyquinazoline수율 73.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Diethyl azodicarboxylate (0.847 g, 4.86 mmol) was added to a solution of 4-(4-fluoro-2-methylindol-5-yloxy)-6-hydroxy-7-methoxyquinazoline (1.5 g, 4.42 mmol), (prepared as described for the starting material in Example 1), triphenylphosphine (1.74 g, 6.63 mmol) and 3-bromo-1-propanol (0.923 g, 6.63 mol) in methylene chloride. After stirring for 1 hour at ambient temperature, triphenylphosphine (1.16 g) and DEAD (0.770 g) was added. After stirring for 30 minutes, the volatiles were removed under vacuum and the residue was purified by column chromatography eluting with increasingly polar mixtures of methylene chloride and ethyl acetate to give 6-(3-bromopropoxy)-4-(4-fluoro-2-methylindol-5-yloxy)-7-methoxyquinazoline (1.5 g, 73%).

후처리

  1. custom(prepared
  2. stirringAfter stirring for 30 minutes
  3. customthe volatiles were removed under vacuum
  4. customthe residue was purified by column chromatography
  5. washeluting
  6. temperaturewith increasingly polar mixtures of methylene chloride and ethyl acetate

출처 및 근거

ORD 기록
ord-7877a5801a174aa1ae5c352d947d5e33
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268230B2

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