Sodium ethoxide → HCID 44467012, compound

HRID 1642463Notes

Reaction equation

HRID 1642463 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[N:8]([C:9](=[O:22])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=1)[C:7]1[CH:23]=[CH:24][CH:25]=[CH:26][C:6]=1[N:5]2[CH3:27].[CH:28]1([CH2:31][O:32][C:33]2[C:40]([O:41][CH3:42])=[CH:39][CH:38]=[CH:37][C:34]=2[CH:35]=O)[CH2:30][CH2:29]1.[O-]CC.[Na+]>C(O)C>[CH:28]1([CH2:31][O:32][C:33]2[C:40]([O:41][CH3:42])=[CH:39][CH:38]=[CH:37][C:34]=2/[CH:35]=[CH:1]/[C:2]2[N:3]=[C:4]3[N:8]([C:9](=[O:22])[C:10]=2[C:11]2[CH:12]=[CH:13][C:14]([O:17][C:18]([F:21])([F:19])[F:20])=[CH:15][CH:16]=2)[C:7]2[CH:23]=[CH:24][CH:25]=[CH:26][C:6]=2[N:5]3[CH3:27])[CH2:29][CH2:30]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 435604072-(Cyclopropylmethoxy)-3-methoxybenzaldehydeHCID 66753238HCID 66753238, compound

Product 1

HCID 44467012HCID 44467012, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was synthesized by condensation of Intermediate 25 (300 mg, 0.801 mmol) with 2-cyclopropylmethoxy-3-methoxy benzaldehyde (215 mg, 1.010 mmol) in presence of sodium ethoxide (108 mg, 1.610 mmol) in ethanol (25 ml) according to the procedure described in Example 24 to afford crude product which was purified by column chromatography to give 416 mg of the desired compound; 1H NMR (300 MHz, DMSO-d6) δ 0.23-0.32 (m, 2H), 0.49-0.56 (m, 2H), 1.12 (br s, 1H), 3.70-3.78 (m, 6H), 3.87 (s, 2H), 6.91-6.99 (m, 3H), 7.20-7.26 (m, 1H), 7.32-7.38 (m, 1H), 7.45-7.54 (m, 5H), 7.68 (d, J=8.4 Hz, 1H), 8.27 (d, J=16.2 Hz, 1H), 8.37-8.43 (m, 1H); APCI-MS (m/z) 562.49 (M+H)+.

Workup

  1. customto afford crude product which
  2. customwas purified by column chromatography

Sources & evidence

ORD record
ord-431f616b7f424a60a18bd2ca8540e93f
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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