Methanol → HCID 57722772, compound

HRID 222258Notes

Reaction equation

HRID 222258 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=O)=[O:9])=[CH:6][C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:4][N:3]=1.CO.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>CCOC(C)=O>[C:18]1([C:5]2[CH:6]=[C:7]3[C:8](=[O:9])[C:10]4[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=4[CH:12]=[CH:1][C:2]3=[N:3][CH:4]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2733832Lithium HexamethyldisilazideHCID 577228102-(2-Methyl-5-phenylpyridine-3-carbonyl)benzaldehyde

Product 1

HCID 57722772HCID 57722772, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A flask was charged with 2-[(2-methyl-5-phenylpyridin-3-yl)carbonyl]benzaldehyde (6.2 mg, 0.02 mmol) and MeOH (1 mL). LiHMDS (25 μl, 1.0 M in THF) was added and the vessel was heated in the Biotage Initiator series microwave for 30 min. at 100° C. The mixture was then diluted with EtOAc, washed with water and brine, then dried over Na2SO4. The solution was concentrated in vacuo and purified by reverse phase HPLC (0-100% CH3CN/water with a 0.1% TFA modifier) to afford the title compound. 1H NMR (600 MHz, CD3OD) δ 9.15 (d, 1H), 8.76 (d, 1H), 8.25 (d, 1H), 7.77 (m, 4H), 7.66 (t, 1H), 7.54 (t, 21), 7.45 (m, 2H0, 7.36 (d, 1H). LRMS (APCI) calculated for C20H14NO [M+H]+, 284.1; found 283.8.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationThe solution was concentrated in vacuo
  4. custompurified by reverse phase HPLC (0-100% CH3CN/water with a 0.1% TFA modifier)

Sources & evidence

ORD record
ord-12c44b1b730f408690494291e1870600
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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