2-Thiophenecarboxaldehyde → HCID 54465784, 화합물

HRID 1418547노트

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HRID 1418547 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[Br:8][C:9]1[C:10]([OH:20])=[C:11]([NH2:19])[C:12](=[C:16]([Br:18])[CH:17]=1)[C:13]([OH:15])=[O:14].[O-]S([O-])(=O)=O.[Na+].[Na+].C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[Br:8][C:9]1[C:10]([OH:20])=[C:11]([NH:19][CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[C:12](=[C:16]([Br:18])[CH:17]=1)[C:13]([OH:15])=[O:14]

참가 물질

7

반응물 4

HCID 73642-ThiophenecarboxaldehydeHCID 24436Sodium SulfateHCID 5003444Sodium cyanoborohydrideHCID 99048002-Amino-4,6-dibromo-3-hydroxybenzoic acid

생성물 1

HCID 54465784HCID 54465784, 화합물수율 12.3%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매2회

실험 절차

A solution of 2-thiophenecarboxaldehyde (38 mg, 0.34 mmol) in dry methanol (0.8 mL) was added to a mixture of 4,6-dibromo-3-hydroxyanthranilic acid (105 mg, 0.34 mmol) and Na2SO4 (240 mg, 1.7 mmol) in methanol (2 mL ). The reaction mixture was stirred overnight at room temperature. Sodium cyanoborohydride (32 mg, 0.51 mmol) was added, and the mixture was stirred for 2 days at room temperature. Conc. acetic acid (1 mL) was added, and the solvent was removed in vacuo. The residue was partitioned between brine and EtOAc (20 mL). The layers were separated and the aqueous layer was extracted with EtOAc (20 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The obtained material was purified by column chromatography (SiO2, CH2Cl2 -hexane-EtOAc-conc. HOAc 30:30:20:3). Preparative HPLC (H2O-acetonitrile-conc. HOAc 50:50:1) yielded the title compound as a yellowish solid (17 mg): 1H NMR (CD3OD-d4) 7.26 (dd, J=5 Hz, 1 Hz), 7.20 (s 1 H), 6.99 (m, 1 H), 6.92 (dd, J=5 Hz, J=5 Hz, 1 H), 4.54 (s, 2 H); MS (TSP): m/z (rel.int.) 410/408/406 (M+1, 5/12/7), 234/232 (31/28), 154 (100).

후처리

  1. stirringthe mixture was stirred for 2 days at room temperature
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between brine and EtOAc (20 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (20 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained material was purified by column chromatography (SiO2, CH2Cl2 -hexane-EtOAc-conc. HOAc 30:30:20:3)

출처 및 근거

ORD 기록
ord-3ea2c05dfe0246c8947606f9d36ac289
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05883129

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