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

HRID 222257

반응식

HRID 222257 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 11194830Cuprous 2-thiophenecarboxylate촉매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-524f2e4b009b4c339680a96be5303e38
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207186B2

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