Water → 1-[2-Bromo-5,6-dichloro-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-indol-3-yl]-ethanone

HRID 28367Notes

Reaction equation

HRID 28367 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[N:7]([C@@H:12]1[O:26][C@H:25]([CH2:27][O:28]C(C3C=CC(C)=CC=3)=O)[C@@H:14]([O:15]C(C3C=CC(C)=CC=3)=O)[CH2:13]1)[C:6]([Br:38])=[C:5]2[C:39](=[O:41])[CH3:40].C[O-].[Na+].O>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[N:7]([C@@H:12]1[O:26][C@H:25]([CH2:27][OH:28])[C@@H:14]([OH:15])[CH2:13]1)[C:6]([Br:38])=[C:5]2[C:39](=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 67099812HCID 67099812, compound

Product 1

HCID 52726201-[2-Bromo-5,6-dichloro-1-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-indol-3-yl]-ethanoneYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5,6-Dichloro-2-bromo-3-acetyl-1-[3,5-di-O-(p-toluoyl)-2-deoxy-β-D-ribofuranosyl]indole (4.142, 1.24 g, 1.7 mmol) was suspended in absolute MeOH (75 mL) to which was added sodium methoxide (250 mg, 4.6 mmol). The suspension was stirred at room temperature for 2 h, after which time the solution first clarified and then a precipitate formed. Water (100 mL) was added, and the suspension was evaporated until no more MeOH remained. The remaining solids were filtered and recrystallized twice from MeOH/H2O to yield 475 mg (68%) of 4.143 as a white crystalline solid: mp slow dec. >235° C.; Rf 0.5 (10% MeOH/CHCl3); 1H-NMR (500 MHz, DMSO-d6): δ 8.57 (s, 1H), 8.37 (s, 1H), 6.56 (dd, 1H), 5.46 (s, 1H, D2O exch.), 5.31 (s, 1H, D2O exch.), 4.48 (d, 1H), 3.92 (d, 1H), 3.76 (s, 2H), 2.65 (s, 3H), 2.48 (m, 1H), 2.13 (ddd, 1H). 13C-NMR (125 MHz, DMSO-d6): δ 192.59, 133.20, 126.74, 125.89, 125.77, 121.91, 121.80, 115.94, 115.32, 87.59, 87.30, 69.84, 60.66, 39.23 (under DMSO), 30.95. HRMS (EI) m/z calcd. for C15H14BrCl2NO4 420.9483, found 420.9493. Anal calcd for C15H14BrCl2NO4: C, 42.58; H, 3.34; N, 3.31. Found: C, 42.77; H, 3.25; N, 3.22.

Workup

  1. customa precipitate formed
  2. customthe suspension was evaporated until no more MeOH
  3. filtrationThe remaining solids were filtered
  4. customrecrystallized twice from MeOH/H2O

Sources & evidence

ORD record
ord-00c1948903594938ad69628f9ee53437
Source dataset
uspto-grants-2008_09
Patent number
US07419963B2

Reaction notes

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