Bromine → HCID 18613734, 화합물

HRID 705112노트

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HRID 705112 반응식
[CH2:1]([C:3]1[N:4]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[N:9][C:7]=2[N:8]=1)[CH3:2].C([O-])(=O)C.[Na+].[Br:26]Br>C(O)(=O)C>[Br:26][CH:1]([C:3]1[N:4]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[N:9][C:7]=2[N:8]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 186137392-Ethyl-3-(4-fluorophenyl)pyrido[2,3-d]pyrimidin-4(3H)-one

생성물 1

HCID 18613734HCID 18613734, 화합물수율 85.1%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

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온도
40 °C

실험 절차

A suspension of the quinazolinone (17) (50.0 g, 0.56 mmol) and anhydrous sodium acetate (56 mg) in glacial acetic acid (1.0 mL) was heated to 40° C. and treated dropwise with a solution of bromine (90 mg, 0.56 mmol) in glacial acetic acid (5 mL). Once the starting material was fully consumed by TLC analysis, the mixture was poured onto water (5 mL), basified with saturated aqueous sodium hydrogen carbonate and extracted with tert-butylmethyl ether. The combined organic phases were dried (MgSO4), filtered, and concentrated to a solid which was purified by silica-gel column chromatography [eluent: Ethyl acetate:Hexane, 50:50, ν/ν] to give the title bromide (18) (166 mg. 85%) as an off white solid:

후처리

  1. customOnce the starting material was fully consumed by TLC analysis
  2. additionthe mixture was poured onto water (5 mL)
  3. extractionextracted with tert-butylmethyl ether
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a solid which
  7. customwas purified by silica-gel column chromatography [eluent: Ethyl acetate:Hexane, 50:50, ν/ν]

출처 및 근거

ORD 기록
ord-fb77320853704d068e98c6db1898b3b2
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173869B2

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