Dimethylformamide → HCID 86035948, compound

HRID 751344Notes

Reaction equation

HRID 751344 reaction equation
P(Cl)(Cl)([Cl:3])=O.CN(C)[CH:8]=[O:9].[S:11]1[CH:15]=[CH:14][C:13]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][C:17]2=O)=[CH:12]1>ClCCl.N1C=CC=CC=1>[Cl:3][C:17]1[N:16]([C:13]2[CH:14]=[CH:15][S:11][CH:12]=2)[C:24]2[C:19]([C:18]=1[CH:8]=[O:9])=[CH:20][CH:21]=[CH:22][CH:23]=2

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 148193781-(Thiophen-3-yl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 86035948HCID 86035948, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

Phosphorous oxychloride (1.9 mL, 20.9 mmol) is added slowly to a stirred solution of dimethylformamide (2 mL) and dichloromethane (2 mL) cooled to 0-5° C. After 5 min a solution of the above 1-(thien-3-yl)-1H-indol-2-one (1.0 g, 2.65 mmol), pyridine (1 mL) and dichloromethane (4 mL) is added and the reaction is stirred at room temperature for 48 hr. The reaction mixture is poured into ice/water and extracted with ethyl acetate. Some solids are removed by filtration and the organic layer is separated, dried, filtered and concentrated. The residue is purified by chromatography eluting with pentane-10% ethyl acetate. Product containing fraction are combined and concentrated to afford 2-chloro-1-(thien-3-yl)-1H-indole-3-carboxaldehyde (694 mg, 57%) as a light orange solid. MS 262 (M+H).

Workup

  1. extractionextracted with ethyl acetate
  2. customSome solids are removed by filtration
  3. customthe organic layer is separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by chromatography
  8. washeluting with pentane-10% ethyl acetate
  9. additionProduct containing fraction
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-7d96ce2a87f44694af38317b0cdf6d5e
Source dataset
uspto-grants-2008_07
Patent number
US07405300B2

Reaction notes

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