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

HRID 132514

反応式

HRID 132514 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21863450Trifluoroacetic acid methylene chloride溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-74797279543b4f0083130ed6ca5b2096
出典データセット
uspto-grants-2008_06
特許番号
US07388012B2

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