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

HRID 222257Notes

Reaction equation

[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

Participants

Conditions

Temperature: 50 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-524f2e4b009b4c339680a96be5303e38
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207186B2

Reaction notes

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