Sodium Acetate → HCID 11535765、化合物

HRID 1919643ノート

反応式

HRID 1919643 の反応式
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9]C)=O.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C([O-])(=O)C.[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[S:3]1[C:2]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[NH:11][C:7](=[O:9])[C:6]=2[CH:5]=[CH:4]1

参加物

6

反応物 3

HCID 517045Sodium AcetateHCID 2773216(2-Aminophenyl)boronic acidHCID 53302196Methyl 2-bromothiophene-3-carboxylate

生成物 1

HCID 11535765HCID 11535765、化合物収率 12%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

In a microwave vessel, methyl 2-bromo-3-thiophene carboxylate (1.0 eq, 64 mg, 0.29 mmol), 2-amino phenyl boronic acid (1.2 eq, 48 mg, 0.35 mmol), sodium acetate (3.0 eq, 71 mg, 0.86 mmol) and PdCl2(dppf) (0.1 eq, 15 mg, 0.028 mmol) were mixed together in anhydrous DMF (0.2 ml). The mixture was heated in a microwave oven at 120° C. for 5 nm. The material was purified by preparative HPLC. Acetonitrile was evaporated, and the compound was extracted with CH2Cl2 (3×). The combined extracts were washed with water, dried over Na2SO4, and the solvents removed in vacuo. Recrystallization in EtOH provided thieno[3,2-c]quinolin-4(5H)-one as a tan crystalline solid (7 mg, 12% yield). LCMS (ES): 95% pure, m/z 202 [M+1]+; 1H NMR (CDCl3/CD3OD, 9:1, 400 MHz) δ 7.28 (m, 1H), 7.33 (m, 1H), 7.43-7.50 (m, 2H), 7.74 (d, J=4.4, 1H), 7.82 (d, J=7.6, 1H) ppm.

後処理

  1. customThe material was purified by preparative HPLC
  2. customAcetonitrile was evaporated
  3. extractionthe compound was extracted with CH2Cl2 (3×)
  4. washThe combined extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvents removed in vacuo
  7. customRecrystallization in EtOH

出典と根拠

ORDレコード
ord-5c592b9cdc154bc5b0f330db9ba85cf6
出典データセット
uspto-grants-2012_05
特許番号
US08168651B2

反応ノート

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