Water → HCID 50941660, 화합물

HRID 604370노트

반응식

HRID 604370 반응식
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

참가 물질

7

반응물 5

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

생성물 1

HCID 50941660HCID 50941660, 화합물수율 48%

시약·촉매·용매 1

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

반응 조건

온도
120 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-240cbed9d6cb4845ac5e980c44c35013
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910600B2

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