Water → HCID 50941659, 화합물

HRID 604363노트

반응식

HRID 604363 반응식
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9]C)=O.Cl.[NH2:12][C:13]1[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=[CH:15][C:14]=1B(O)O.C([O-])(=O)C.[Na+].O>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]>[O:9]=[C:7]1[C:6]2[CH:5]=[CH:4][S:3][C:2]=2[C:14]2[CH:15]=[CH:16][C:17]([C:19]([O:21][CH3:22])=[O:20])=[CH:18][C:13]=2[NH:12]1

참가 물질

7

반응물 4

HCID 962WaterHCID 517045Sodium AcetateHCID 164270832-Amino-4-(methoxycarbonyl)benzeneboronic acid hydrochlorideHCID 53302196Methyl 2-bromothiophene-3-carboxylate

생성물 1

HCID 50941659HCID 50941659, 화합물수율 50%

시약·촉매·용매 2

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

반응 조건

온도
120 °C

실험 절차

In a microwave vessel, methyl 2-bromo-3-thiophene carboxylate (1.0 eq, 260 mg, 1.18 mmol), 2-amino-4-(methoxycarbonyl)phenylboronic acid hydrochloride (1.1 eq, 300 mg, 1.30 mmol), sodium acetate (3.0 eq, 292 mg, 3.56 mmol) and PdCl2(dppf) (0.05 eq, 31 mg, 0.059 mmol) were mixed together in anhydrous DMF (2 ml). The mixture was heated in a microwave oven at 120° C. for 10 nm. Water was added and the solid filtered and dried. The material was suspended in CH2Cl2, filtered and dried to afford methyl 4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carboxylate as a yellow solid (152 mg, 50% yield). LCMS (ES): 95% pure, m/z 260 [M+1]+; 1H NMR (CDCl3, 400 MHz) δ 3.99 (s, 3H), 7.54 (d, J=5.2, 1H), 7.79 (d, J=4.8, 1H), 7.86 (d, J=8.4, 1H), 7.91 (dd, J=8.4, J=1.6, 1H), 8.03 (d, J=1.2, 1H) ppm.

후처리

  1. filtrationthe solid filtered
  2. customdried
  3. filtrationfiltered
  4. customdried

출처 및 근거

ORD 기록
ord-7d4e08153f7044739b84585dcbd2a6b9
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910600B2

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