Triethylamine → HCID 53907499, compound

HRID 1387419Notes

Reaction equation

HRID 1387419 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([Br:23])[C:21]=1[OH:22])[CH:5]=[C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15](O)=[O:16])[CH:13]=2)[NH:8][C:7]1=[O:18].C(P(=O)([O:30][CH2:31][CH3:32])OCC)#N.C([N:36](CC)CC)C>CN(C=O)C>[OH:30][CH2:31][CH2:32][NH:36][C:15]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:18])[C:6]2=[CH:5][C:4]1[CH:19]=[C:20]([Br:23])[C:21]([OH:22])=[C:2]([Br:1])[CH:3]=1)=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 53930872HCID 53930872, compound

Product 1

HCID 53907499HCID 53907499, compoundYield 5.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

3-(3,5-Dibromo-4-hydroxy-benzylidene)-2-oxo-2,3-dihydro-1H-indol-5-carboxylic acid (0.34 9, 0.77 mmol) (Example 156) and ethanofamine (0.08 g, 1.3 mmol) were dissolved in DMF (2 mL) and cooled with stirring to 5° C. Diethyl cyanophosphonate (0.172 g, 1 mmol), followed by triethylamine (0.25 g, 2.5 mmol) were added and stirring continued for 0.5 h at 50° C. and then the reaction allowed to warm to room temperature. After 1.5 h the reaction was quenched with water (10 mL) and extracted four times with a 4/1 mixture of chloroform/isopropanol (25 mL). The organic phases were combined, dried over magnesium sulfate and concentrated to dryness. Recrystalization from ethanol gave 22 mg of 3-(3,5-dibromo-4-hydroxy-benzylidene)-2-oxo-2,3-dihydro-1H-indol-5-carboxylic acid (2-hydroxyethyl)amide; 1H-NMR (DMSO-d6): δ10.9 (s, 1H), 10. 7 (bs, 1H), 8.81 (s, 2H), 8.25 (t, J=5.6 Hz, 1H), 8.19 (s, 1H), 7.77 (s, 1H), 7.72 (d, J=8.0 Hz, 1 H), 6.86 (d, J=8.0 Hz, 1 H), 4.73 (bs, 1H), 3.52 (m, 2H), 3.37 (m, 2H). Mass spectrum (negative ion electrospray): m/z=479 (M−1, 22%), 481 (M−1, 35%), 483 (M−1, 30%).

Workup

  1. temperaturecooled
  2. additionwere added
  3. stirringstirring
  4. temperatureto warm to room temperature
  5. customAfter 1.5 h the reaction was quenched with water (10 mL)
  6. extractionextracted four times
  7. additionwith a 4/1 mixture of chloroform/isopropanol (25 mL)
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated to dryness
  10. customRecrystalization from ethanol

Sources & evidence

ORD record
ord-74a07ebf2f674ba8af25279149eb0275
Source dataset
uspto-grants-2001_07
Patent number
US06268391B1

Reaction notes

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