Water → HCID 11223774, compound

HRID 1837858Notes

Reaction equation

HRID 1837858 reaction equation
[Br:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([C@H:18]([CH3:22])[CH2:19][CH:20]=[O:21])=[C:8]2[CH3:23])=[CH:4][CH:3]=1.[OH-:26].[Na+].O>C(O)C.[N+]([O-])([O-])=O.[Ag+]>[Br:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([C@H:18]([CH3:22])[CH2:19][C:20]([OH:26])=[O:21])=[C:8]2[CH3:23])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 11211734HCID 11211734, compound

Product 1

HCID 11223774HCID 11223774, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 702EthanolSolvent2×

Procedure

A solution of (R)-3-[1-(4-Bromo-benzyl)-5-methoxy-2-methyl-1H-indol-3-yl]-butanal (110 mg, 0.250 mmol) and silver nitrate (59.7 mg, 0.275 mmol) in 1.3 ml absolute ethanol was treated with a solution of 5N NaOH in ethanol (1:5, 0.9 ml, 0.75 mmol NaOH). After 45 min this was treated with 10 ml water, acidified to pH 3 and extracted with CHCl3 (5×20 ml) rinsing each extract with brine. The combined organics were dried over Na2SO4 and concentrated in vacuo to provide, after silica gel chromatography the title compound as a pale yellow solid (101 mg, 97% yield). IR (film) 3425, 2961, 2934, 2833, 1706, 1483, 1451, 1405, 1228, 1156, 1010, 796, 755 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.36 (d, J=9.0 Hz, 2H, ArH), 7.11 (d, J=2.4 Hz, 1H, ArH), 7.04 (d, J=8.7, 1H, ArH), 6.77-6.73 (m, 3H, ArH), 5.18 (s, 2H NCH2), 3.86 (s, 3H, OCH3) 3.56 (dt, J=7.2, 21.9 Hz, 1H ArCH), 2.86 (d, J=3.6 Hz, 1H, CH2CO); 2.83 (d, J=3.3 Hz, 1H, CH2CO); 2.27 (s, 3H, ArCH3) 1.49 (d, J=7.2 Hz, 3H, CHCH3); 13C NMR (75 MHz, CDCl3) δ 178.0, 153.7, 137.3, 133.8, 133.0, 132.0, 127.7, 126.7, 121.2, 118.8, 114.6, 110.1, 109.9, 102.4, 56.3, 46.3, 41.5, 28.6, 21.1, 10.9; HRMS (CI) exact mass calcd for (C21H23BrNO3) (M+1) requires m/z 416.0861, found m/z 416.0867. [α]D=−30.9 (c=1.0, CHCl3).

Workup

  1. extractionextracted with CHCl3 (5×20 ml)
  2. washrinsing
  3. extractioneach extract with brine
  4. dry with materialThe combined organics were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto provide

Sources & evidence

ORD record
ord-3453b515b52744d79ef4fad83b8df5ee
Source dataset
uspto-grants-2004_08
Patent number
US06784323B2

Reaction notes

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