Thionyl Chloride → HCID 59454946, compound

HRID 1400652Notes

Reaction equation

HRID 1400652 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)(O)[CH:13]([CH3:15])[CH3:14])[C:6]3[CH2:23][CH2:24][N:25]([CH3:27])[CH2:26][C:5]=3[C:4]=2[CH:3]=1.S(Cl)(Cl)=O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:13]([CH3:15])[CH3:14])[C:6]3[CH2:23][CH2:24][N:25]([CH3:27])[CH2:26][C:5]=3[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 49779519HCID 49779519, compound

Product 1

HCID 59454946HCID 59454946, compoundYield 18.5%

Procedure

1-(8-Chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)-3-methyl-2-(pyridin-4-yl)butan-2-ol (0.668 g, 1.77 mmol) was dissolved in thionyl chloride (0.32 mL, 2.5 eq) and the solution was stirred at RT for 12 h. Volatiles were removed under reduced pressure, the residue was basified with saturated aqueous sodium bicarbonate, and the product was extracted with EtOAc (3×50 mL). Combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified silica gel chromatography (100-200 mesh) eluting with 5% MeOH:DCM to obtain 0.120 g of product. 1H NMR (DMSO-d6, oxalate salt) δ (ppm): 8.22 (d, 2H), 7.40 (s, 1H), 7.25 (d, 1H), 7.05 (d, 1H), 7.85 (d, 2H), 5.18 (s, 2H), 4.22 (m, 2H), 3.45 (m, 2H), 2.95 (m, 2H), 2.82 (s, 3H), 2.10 (s, 3H), 1.50 (s, 3H).

Workup

  1. customVolatiles were removed under reduced pressure
  2. extractionthe product was extracted with EtOAc (3×50 mL)
  3. dry with materialCombined organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified silica gel chromatography (100-200 mesh)
  6. washeluting with 5% MeOH

Sources & evidence

ORD record
ord-c3359ef161e74346934f3c8697715c87
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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