Water → HCID 23003407, compound

HRID 396450Notes

Reaction equation

HRID 396450 reaction equation
[C:1]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1[CH2:18][C:19](O)=[O:20])=[CH:15][CH:14]=[C:13]([Cl:22])[CH:12]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(C#N)(=O)(OCC)O[CH2:25]C.C([N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])C.O>CN(C=O)C>[C:1]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1[CH2:18][C:19]([N:35]1[CH2:36][CH2:37][CH2:25][CH2:39][CH2:38]1)=[O:20])=[CH:15][CH:14]=[C:13]([Cl:22])[CH:12]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 9819110HCID 9819110, compound

Product 1

HCID 23003407HCID 23003407, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2-benzoyl-6-chloro-1H-indol-3-yl)acetic acid (Example 2, 200 mg, 0.64 mmol), diethyl phosphorocyanidate (DEPC, 0.12 ml, 0.76 mmol) and triethylamine (0.11 ml, 0.76 mmol) in DMF (3.0 ml) was stirred at room temperature for 5 min. The mixture was then poured into water (20 ml) and the orange precipitates were collected by filtration to give 20 mg (11%) of the title compound as orange solids.

Workup

  1. customthe orange precipitates
  2. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-8bd0938926aa45bfbb0d14ec39fc6e9d
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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