Vinyl ether → 1-[5-Benzyloxy-7-(1-ethoxyvinyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea

HRID 712286ノート

反応式

HRID 712286 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](Br)[C:12]2[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=2[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:30]([O:32][CH2:33][CH3:34])=[CH2:31])CCC.C(OC=C)=C>CN(C=O)C.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>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:30]([O:32][CH2:33][CH3:34])=[CH2:31])[C:12]2[S:16][C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:14][C:13]=2[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 8024Vinyl etherHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 578136291-(5-Benzyloxy-7-bromo-benzothiazol-2-yl)-3-ethyl-urea

生成物 1

HCID 866639991-[5-Benzyloxy-7-(1-ethoxyvinyl)-1,3-benzothiazol-2-yl]-3-ethyl-urea

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

1-(5-benzyloxy-7-bromo-1,3-benzothiazol-2-yl)-3-ethyl-urea (1 g, 2.46 mmol) and tributyl-(1-ethoxy-vinyl)-stannane (1.77 g, 4.92 mmol) were dissolved in DMF (30 mL) and the mixture deoxygenated by bubbling N2 through the solution for 20 min. Pd(PPh3)4, (284 mg, 0.246 mmol) was added and the reaction heated to 100° C. for 4 h under a N2 atmosphere, at the end of which time LCMS indicated clean formation of the vinyl ether. The reaction was concentrated under reduced pressure, diluted with EtOAc, washed with water then brine and the organic layer dried (MgSO4), filtered and the solvent removed in vacuo to give the desired compound.

後処理

  1. customthe mixture deoxygenated
  2. customby bubbling N2 through the solution for 20 min
  3. concentrationThe reaction was concentrated under reduced pressure
  4. additiondiluted with EtOAc
  5. washwashed with water
  6. dry with materialbrine and the organic layer dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-6274cc00a01c4548bb0bda619ffba435
出典データセット
uspto-grants-2015_11
特許番号
US09181234B2

反応ノート

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