Sodium Hydroxide → HCID 10202580, compound

HRID 1766251Notes

Reaction equation

HRID 1766251 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[S:11](Cl)(=[O:13])=[O:12].[F:15][C:16]1[CH:24]=[C:23]2[C:19]([C:20]([CH:25]3[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]3)=[CH:21][NH:22]2)=[CH:18][C:17]=1[OH:32]>C1COCC1>[F:15][C:16]1[CH:24]=[C:23]2[C:19]([C:20]([CH:25]3[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]3)=[CH:21][NH:22]2)=[CH:18][C:17]=1[O:32][S:11]([C:5]1[C:6]([F:10])=[CH:7][CH:8]=[CH:9][C:4]=1[F:3])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27342712,6-Difluorobenzenesulfonyl chlorideHCID 17980101HCID 17980101, compound

Product 1

HCID 10202580HCID 10202580, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By a method similar to Example 31, using 0.2N sodium hydroxide (2.4 mmol, 12.2 mL), 2,6-difluorobenzenesulfonyl chloride (2.9 mmol, 0.625 g), 6-fluoro-3-(1-methylpiperidin-4-yl)-1H-indole-5-ol (2.4 mmol, 0.608 g) in THF (7.7 mL). The crude isolated product was subjected to normal phase silica gel radial chromatography, 4 mm plate eluting with 9:1 methylene chloride:2M ammonia in methanol at 10 mL/minute. Fractions containing product combined, concentrated in vacuo to a white solid. The title compound was crystallized from methylene chloride to afford 0.282 g (27%) of the title compound: mp=202° C.; Mass spectrum (ion spray): m/z=425 (M+1); 1H NMR (DMSOd6): 11.10 (s, 1H), 7.91 (m, 1H), 7.40 (m, 2H), 7.26-7.16 (m, 3H), 2.78 (m, 2H), 2.52 (m, 1H), 2.20 (s, 3H), 1.96 (m, 2H), 1.69 (m, 2H), 1.51 (m, 2H); Calculated for C20H19F3N2O3S: C, 56.12; H, 4.57; N, 6.54. Found: C, 56.13; H, 4.56; N, 6.48.

Workup

  1. customThe crude isolated product
  2. washeluting with 9:1 methylene chloride
  3. additionFractions containing product
  4. concentrationconcentrated in vacuo to a white solid
  5. customThe title compound was crystallized from methylene chloride

Sources & evidence

ORD record
ord-ae97beea5cb14ef58be53c2c8c02c5af
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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