Phosphorus oxychloride → HCID 16751083, compound

HRID 1194352Notes

Reaction equation

HRID 1194352 reaction equation
P(Cl)(Cl)(Cl)=O.[F:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[CH:11]=[CH:10]2.[CH3:17][C:18](N(C)C)=[O:19]>>[F:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[CH:11]=[C:10]2[C:18](=[O:19])[CH3:17]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 31374Dimethylacetamide2×HCID 47778355-fluoro-1-methylindole

Product 1

HCID 16751083HCID 16751083, compound

Procedure

Phosphoryl chloride (1.1 ml) was added dropwise to ice-cooled dimethylacetamide (10 ml) and the resulting solution was stirred at ca.0° for 10 min. A solution of 5-fluoro-1-methyl-1H-indole (1.3 g) in dimethylacetamide (5 ml) was added, and the resulting solution was stirred at 100° for 2 h, then cooled, and partitioned between sodium carbonate (2N; 100 ml) and ethyl acetate (2×50 ml). The combined organic extracts were washed with water (50 ml), dried and evaporated in vacuo to give a solid which was purified by FCC eluting with hexane:ethyl acetate (1:1) to give the title compound (0.48 g), m.p. 158°-160°.

Workup

  1. stirringthe resulting solution was stirred at 100° for 2 h
  2. temperaturecooled
  3. custompartitioned between sodium carbonate (2N; 100 ml) and ethyl acetate (2×50 ml)
  4. washThe combined organic extracts were washed with water (50 ml)
  5. customdried
  6. customevaporated in vacuo
  7. customto give a solid which
  8. customwas purified by FCC
  9. washeluting with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-23a3856184c741e0802aaf50b4ccbd01
Source dataset
uspto-grants-1989_03
Patent number
US04814344

Reaction notes

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