Triethylsilane → Methyl 3-[(quinolin-4-ylmethyl)amino]thiophene-2-carboxylate

HRID 132514

반응식

HRID 132514 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH2:10])=[O:4].[N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH:21]=O)=[CH:13][CH:12]=1.C([SiH](CC)CC)C.[OH-].[Na+].C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl.C(Cl)Cl>[N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH2:21][NH:10][C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:3]([O:2][CH3:1])=[O:4])=[CH:13][CH:12]=1

참가 물질

8

반응물 5

HCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 780724-QuinolinecarboxaldehydeHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 516892Sodium Bicarbonate

생성물 1

HCID 59734303Methyl 3-[(quinolin-4-ylmethyl)amino]thiophene-2-carboxylate

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21863450Trifluoroacetic acid methylene chloride용매

반응 조건

온도
50 °C

실험 절차

A mixture of 3-amino-thiophene-2-carboxylic acid methyl ester (5 g, 31.8 mmol) and 4-quinoline-carboxaldehyde (5.25 g, 33.4 mmol) in TFA/CH2Cl2 (75 mL, 75 mL) was heated at 50° C. for 3.5 h. The solution was cooled in an ice bath and triethylsilane (10.2 mL, 63.6 mmol) was added drop-wise over 5 min. The reaction mixture was stirred at 50° C. for 3.5 h, cooled to rt, and 500 mL of CH2Cl2 was added. The reaction mixture was basified with 10N NaOH (pH 6-7) followed by sat. NaHCO3 (pH 8). The CH2Cl2 layer was separated and the aqueous layer was extracted with CH2Cl2 (2×100 mL). The organic extracts were combined, washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to yield the crude product, which was triturated with hexane to give pure methyl 3-[(quinolin-4-ylmethyl)amino]thiophene-2-carboxylate as white solid. MS (ES): m/z 298.55 (100) [MH+]; 1H-NMR (400 MHz/CDCl3): δ 3.87 (s, 3H), 5.00 (d, J=4.0 Hz, 2H), 6.48 (d, J=5.6 Hz, 1H), 7.30 (d, J=5.6 Hz, 1H), 7.36 (m, 1H), 7.41 (d, J=4.4 Hz, 1H), 7.62 (t, J=8.0 Hz, 1H), 7.76 (t, J=9.6 Hz, 1H), 8.01 (d, J=8.0 Hz, 1H), 8.17 (d, J=8.4 Hz, 1H), 8.86 (d, J=4.4 Hz, 1H).

후처리

  1. temperatureThe solution was cooled in an ice bath
  2. temperaturecooled to rt
  3. customThe CH2Cl2 layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (2×100 mL)
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto yield the crude product, which
  10. customwas triturated with hexane

출처 및 근거

ORD 기록
ord-74797279543b4f0083130ed6ca5b2096
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07388012B2

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