5-Fluoroindole-2-carboxylic acid → HCID 59529931, compound

HRID 1894954Notes

Reaction equation

HRID 1894954 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1.[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([C:20](O)=[O:21])=[CH:14]2.ON1C2C=CC=CC=2N=N1.N=C=N.C(=O)([O-])[O-].[N-]=C=O>CN(C=O)C>[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([C:20]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][OH:9])[CH2:3][CH2:2]1)=[O:21])=[CH:14]2

Participants

8

Reactant 6

HCID 18205-Fluoroindole-2-carboxylic acidHCID 19660Carbonate IonHCID 739534-PiperidineethanolHCID 757711-HydroxybenzotriazoleHCID 105034IsocyanateHCID 160435Carbodiimide

Product 1

HCID 59529931HCID 59529931, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4.1 mg of 4-piperidine ethanol, 5.3 mg of 5-fluoro-1H-indole-2-carboxylic acid, and 4.0 mg of 1-hydroxybenzotriazole in 0.6 mL of DMF was added 100 mg of PS-Carbodiimide (Argonaut Technologies) at room temperature, followed by stirring overnight. To the reaction liquid were added 50 mg of MP-Carbonate (Argonaut Technologies) and 50 mg of PS-Isocyanate (Argonaut Technologies) at room temperature, followed by stirring for 2 hours, and insoluble material was filtered. The filtrate was concentrated under reduced pressure to obtain 8.8 mg of 2-{1-[(5-fluoro-1H-indol-2-yl)carbonyl]piperidin-4-yl}ethanol.

Workup

  1. customTo the reaction liquid
  2. stirringby stirring for 2 hours
  3. filtrationinsoluble material was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c15474c675f24a34ad15bb0d55ae67ae
Source dataset
uspto-grants-2013_08
Patent number
US08513422B2

Reaction notes

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