Triethylamine → HCID 178516145、化合物

HRID 577089ノート

反応式

HRID 577089 の反応式
Br[CH2:2][C:3]1[C:4]([Cl:10])=[N:5][CH:6]=[CH:7][C:8]=1[Cl:9].[SH:11][C:12]1[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([C:19]([F:22])([F:21])[F:20])[N:13]=1.C(N(CC)CC)C>C(O)C>[Cl:10][C:4]1[C:3]([CH2:2][S:11][C:12]2[N:17]=[C:16]([OH:18])[CH:15]=[C:14]([C:19]([F:22])([F:20])[F:21])[N:13]=2)=[C:8]([Cl:9])[CH:7]=[CH:6][N:5]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 589517013-(Bromomethyl)-2,4-dichloropyridineHCID 178516148HCID 178516148、化合物

生成物 1

HCID 178516145HCID 178516145、化合物収率 22%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 3-(bromomethyl)-2,4-dichloropyridine (2.9 g, 12.3 mmol), 2-sulfanyl-6-(trifluoromethyl)pyrimidin-4-ol (1.2 g, 6.1 mmol), and triethylamine (1.3 mL, 9.3 mmol) in absolute ethanol (25 mL) was stirred at room temperature overnight. The mixture was evaporated to dryness. The residue was dissolved in EtOAc (80 mL). The solution was extracted with water (3×50 mL) and 1 N NaOH (1×50 mL). The organic layer was recovered, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-5% MeOH/DCM), affording the title compound (475 mg, 22% yield); 1H NMR (400 MHz, DMSO-d6): δ 4.75 (s, 2H), 6.72 (s, 1H), 7.69 (d, 1H, J=5.3 Hz), 8.36 (d, 1H, J=5.3 Hz); M+ 357.

後処理

  1. customThe mixture was evaporated to dryness
  2. dissolutionThe residue was dissolved in EtOAc (80 mL)
  3. extractionThe solution was extracted with water (3×50 mL) and 1 N NaOH (1×50 mL)
  4. customThe organic layer was recovered
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customdried in vacuo
  9. customThe crude product was purified by flash chromatography (0-5% MeOH/DCM)

出典と根拠

ORDレコード
ord-6ec295a479f049ca865a42dad51fc2ef
出典データセット
uspto-grants-2015_05
特許番号
US09040538B2

反応ノート

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