Sodium Acetate → HCID 11535765, 화합물

HRID 604369노트

반응식

HRID 604369 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 11535765HCID 11535765, 화합물수율 12%

시약·촉매·용매 2

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

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온도
120 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-1bc109be9931464280e4f35a9dcd0aa9
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910600B2

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