Ammonia → HCID 86707945, compound

HRID 2400293Notes

Reaction equation

HRID 2400293 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:8]2[CH2:11][C:12]2[O:16][C:15]([C:17](OCC)=[O:18])=[CH:14][CH:13]=2)=[CH:4][C:3]=1[O:28][CH3:29].[NH3:30]>>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:8]2[CH2:11][C:12]2[O:16][C:15]([C:17]([NH2:30])=[O:18])=[CH:14][CH:13]=2)=[CH:4][C:3]=1[O:28][CH3:29]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 67684772HCID 67684772, compound

Product 1

HCID 86707945HCID 86707945, compound

Procedure

A suspension of ethyl 5-(6-chloro-5-methoxy-2-phenylindol-1-ylmethyl)furan-2-carboxylate (258 mg) in ammonia (Ca. 7 mol/L methanol solution, 12.4 mL) was stirred at room temperature for 44 hours. The reaction mixture was filtered, washed with methanol, and then concentrated under reduced pressure to obtain the title compound (138 mg). 1H-NMR (CDCl3) δ ppm: 3.95 (3H, s), 5.23 (2H, s), 6.10 (1H, d, J=3.5 Hz), 6.50-6.55 (1H, m), 7.03 (1H, d, J=3.5 Hz), 7.15 (1H, s), 7.35-7.55 (6H, m).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with methanol
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4dbe9a2bb4b49498f5ec2ce5ad1a304
Source dataset
uspto-grants-2014_08
Patent number
US08796247B2

Reaction notes

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