2-Formylphenylboronic acid → 2-(2-Methyl-5-phenylpyridine-3-carbonyl)benzaldehyde

HRID 222257

反応式

HRID 222257 の反応式
[CH3:1][C:2]1[C:7]([C:8](=[O:17])SC2C=CC(C)=CC=2)=[CH:6][C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:4][N:3]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.[CH:40]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1B(O)O)=[O:41]>S1C=CC=C1C([O-])=O.[Cu+]>[CH3:1][C:2]1[C:7]([C:8]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[CH:40]=[O:41])=[O:17])=[CH:6][C:5]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 2921892-Formylphenylboronic acidHCID 521585Tris(furan-2-yl)phosphaneHCID 57722887S-(4-methylphenyl) 2-methyl-5-phenylpyridine-3-carbothioate

生成物 1

HCID 577228102-(2-Methyl-5-phenylpyridine-3-carbonyl)benzaldehyde

試薬・触媒・溶媒 1

HCID 11194830Cuprous 2-thiophenecarboxylate触媒

反応条件

温度
50 °C

実験手順

S-(4-methylphenyl) 2-methyl-5-phenylpyridine-3-carbothioate (100 mg, 0.31 mmol), copper (I) thiophene-2-carboxylate (89.6 mg, 0.47 mmol), Pd2 dba3CHCl3 (26 mg, 0.025 mmol), tri-2-furylphosphine (17.3 mg, 0.074 mmol) and 2-formylphenylboronic acid (51.7 mg, 0.34 mmol) were combined in a dry flask. The flask was purged with argon and 3.0 mL of THF were added. Argon was bubbled through the solution for 5 minutes and the solution was stirred and heated to 50° C. After 18 hours, the reaction mixture was diluted with EtOAc, washed with 1N HCl, brine, dried over sodium sulfate, filtered, concentrated and purified by flash chromatography (100-70% hexanes/EtOAc gradient) to afford the title compound. LRMS (APCI) calculated for C20H16NO2 [M+H]+, 302.1; found 302.1.

後処理

  1. customThe flask was purged with argon and 3.0 mL of THF
  2. additionwere added
  3. customArgon was bubbled through the solution for 5 minutes
  4. additionthe reaction mixture was diluted with EtOAc
  5. washwashed with 1N HCl, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash chromatography (100-70% hexanes/EtOAc gradient)

出典と根拠

ORDレコード
ord-524f2e4b009b4c339680a96be5303e38
出典データセット
uspto-grants-2012_06
特許番号
US08207186B2

関連ノート

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