Cesium carbonate → Methyl 3-hexylquinoline-8-carboxylate

HRID 472791ノート

反応式

HRID 472791 の反応式
FC(F)(F)S(O[C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][C:11]=2[C:17]([O:19][CH3:20])=[O:18])(=O)=O.[CH2:23](B(O)O)[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:23]([C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][C:11]=2[C:17]([O:19][CH3:20])=[O:18])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 351064Hexylboronic Acid (contains varying amounts of Anhydride)HCID 58056975Methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylate

生成物 1

HCID 66660858Methyl 3-hexylquinoline-8-carboxylate収率 41%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
95 °C

実験手順

Methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylate (538 mg, 1.6 mmol), hexylboronic acid (415 mg, 3.2 mmol) and Cs2CO3 (779 mg, 2.4 mmol) were suspended in toluene (30 mL). The mixture was purged with nitrogen then tetrakis(triphenylphosphine)palladium (0) (55 mg, 0.05 mmol) was added. The reaction was sealed and heated at 95° C. for 16 h. The mixture was cooled and filtered through celite, rinsing with excess CH2Cl2. The filtrate was concentrated in vacuo. The resulting oil was purified on 40 g silica gel (19:1 CH2Cl2/methyl t-butyl ether) to afford 178 mg (41%) of methyl 3-hexylquinoline-8-carboxylate.

後処理

  1. customThe mixture was purged with nitrogen
  2. customThe reaction was sealed
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through celite
  5. washrinsing with excess CH2Cl2
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe resulting oil was purified on 40 g silica gel (19:1 CH2Cl2/methyl t-butyl ether)

出典と根拠

ORDレコード
ord-c7de980b234a48279a603d7e7bc23c14
出典データセット
uspto-grants-2014_01
特許番号
US08633220B2

反応ノート

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