Water → HCID 50941660、化合物

HRID 604370ノート

反応式

HRID 604370 の反応式
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9]C)=O.Cl.N[C:13]1[C:18]([C:19]#[N:20])=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.C([O-])(=O)C.[Na+].O.C[N:31](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]>[O:9]=[C:7]1[C:6]2[CH:5]=[CH:4][S:3][C:2]=2[C:15]2[CH:16]=[CH:17][C:18]([C:19]#[N:20])=[CH:13][C:14]=2[NH:31]1

参加物

7

反応物 5

HCID 962WaterHCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 53302196Methyl 2-bromothiophene-3-carboxylateHCID 670388782-amino-3-cyanophenyl boronic acid HCl

生成物 1

HCID 50941660HCID 50941660、化合物収率 48%

試薬・触媒・溶媒 1

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

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, 250 mg, 1.13 mmol), 2-amino-3-cyanophenyl boronic acid HCl (1.1 eq, 250 mg, 1.24 mmol), sodium acetate (3.0 eq, 278 mg, 3.39 mmol) and PdCl2(dppf) (0.007 eq, 4.3 mg, 0.0082 mmol) were mixed together in anhydrous DMF (2.5 ml). The mixture was heated in a microwave oven at 120° C. for 10 nm. Water was added and the material extracted with CH2Cl2. The organic extracts were washed with brine, dried over Na2SO4 and the solvents removed in vacuo. The resulting solid was sonicated in AcOEt, filtered and dried to afford 4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carbonitrile as a beige solid (121 mg, 48% yield). LCMS (ES): 95% pure, m/z 227 [M+1]+.

後処理

  1. extractionthe material extracted with CH2Cl2
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customthe solvents removed in vacuo
  5. customThe resulting solid was sonicated in AcOEt
  6. filtrationfiltered
  7. customdried

出典と根拠

ORDレコード
ord-240cbed9d6cb4845ac5e980c44c35013
出典データセット
uspto-grants-2011_03
特許番号
US07910600B2

反応ノート

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