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Cesium carbonate → HCID 69270317, 화합물

HRID 1795343
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HRID 1795343 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]2[C:7](=[C:8](Br)[CH:9]=[C:10]([F:17])[CH:11]=2)[N:6]=1)=[O:4].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:65][N:66]1[CH2:71][CH2:70][NH:69][CH2:68][CH2:67]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]2[C:7](=[C:8]([N:69]3[CH2:70][CH2:71][N:66]([CH3:65])[CH2:67][CH2:68]3)[CH:9]=[C:10]([F:17])[CH:11]=2)[N:6]=1)=[O:4]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 634876Binap, (A+-)-HCID 53419807Methyl 8-bromo-6-fluoro-4-methoxyquinoline-2-carboxylate

생성물 1

HCID 69270317HCID 69270317, 화합물수율 90%

시약·촉매·용매 1

HCID 1140
Toluene
용매

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온도
80 °C

실험 절차

Into a 250 mL, 3 neck round bottom flask equipped with a reflux condenser, magnetic stirrer and nitrogen inlet is added 2.1 g (6.68 mmol, 1.0 equiv.) of 8-Bromo-6-fluoro-4-methoxy-quinoline-2-carboxylic acid methyl ester (Reference Example 29a) (122 mg, 0.134 mmol, 0.02 equiv.) of tris dibenzylidineacetone dipalladium, 499 mg (0.802 mmol, 0.12 equiv.) of racemic 2,2′-bis(diphenylphosphino)-1,1′-binapthyl and 1 g of 4 A molecular sieves and 80 mL of dry toluene. To the stirred suspension is then added 736 mg, 815 μL, (7.35 mmol, 1.1 equiv.) of 1-methylpiperazine, followed by 3.05 g (9.35 mmol, 1.4 equiv.) of cesium carbonate. The mixture is then heated to 80° C. for 36 hr. At the end of this time completion was monitored by LC/MS analysis of an aliquot. When the reaction was determined to be complete it was cooled to room temperature then filtered through a plug of celite, with toluene washing to remove solid by products. Purification by flash chromatography using a gradient of 5 to 20% methanol in methylene chloride as eluent yielded 2.0 g, (90%) of the desired product. Mass Spec.: calc. for [C17H20FN3O3+H]+ Theor. m/z=334; Obs.=334

후처리

  1. customInto a 250 mL, 3 neck round bottom flask equipped with a reflux condenser, magnetic stirrer and nitrogen inlet
  2. temperaturewas cooled to room temperature
  3. filtrationthen filtered through a plug of celite, with toluene washing
  4. customto remove solid by products
  5. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-6dcc8c4f4b254db495eb0898938b6ed1
출처 데이터셋
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07026314B2

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