Pyridine → HCID 68865000, compound

HRID 1725895Notes

Reaction equation

HRID 1725895 reaction equation
[NH2:1][C:2]1[C:10]([C:11]([O:13]CC)=[O:12])=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C:16]1([S:26](Cl)(=[O:28])=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.N1C=CC=CC=1.[Li+].[OH-]>C(Cl)Cl>[C:16]1([S:26]([NH:1][C:2]2[C:10]([C:11]([OH:13])=[O:12])=[C:9]3[C:5]([CH:6]=[CH:7][NH:8]3)=[CH:4][CH:3]=2)(=[O:28])=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 3939Lithium HydroxideHCID 665601-Naphthalenesulfonyl chlorideHCID 10822051Ethyl 6-amino-1H-indole-7-carboxylate

Product 1

HCID 68865000HCID 68865000, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 6-amino-1H-indole-7-carboxylate (prepared as described in Showalter, H. D. et al., J. Org. Chem., 1996, 61, 1155-1158, 0.05 g, 0.25 mmol) in CH2Cl2 (5 mL) was treated with 1-naphthalenesulfonyl chloride (0.066 g, 0.29 mmol) and pyridine (0.040 mL, 0.50 mmol), shaken for 16 hours at ambient temperature, filtered, and concentrated. The concentrate was dissolved in 9:1 methanol/water (1 mL), treated with LiOH (25 mg, 0.6 mmol), and heated to 60° C. for 16 hours. The mixture was concentrated and the concentrate was purified by C18 reverse-phase HPLC using acetonitrile/water/0.1% TFA to provide the desired product. MS (DCI) m/e 384 (M+NH4)+; 1H NMR (500 MHz, DMSO-d6) δ 12.43 (br s, 1H), 10.77 (s, 1H), 8.62 (d, 1H), 8.30 (dd, 1H), 8.18 (d, 1H), 8.03 (d, 1H), 7.69 (m, 1H), 7.64-7.60 (m, 3H), 7.20 (d, 1H), 7.17 (t, 1H), 6.35 (dd, 1H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. dissolutionThe concentrate was dissolved in 9:1 methanol/water (1 mL)
  4. temperatureheated to 60° C. for 16 hours
  5. concentrationThe mixture was concentrated
  6. customthe concentrate was purified by C18 reverse-phase

Sources & evidence

ORD record
ord-36d9f452358249f7ab716682197933b4
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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