Sodium Hydroxide → 2-(3-Cyano-4-(5-(2,4-dichlorophenethylcarbamoyl)-1H-indol-1yl)phenyl)acetic Acid

HRID 1810103Notes

Reaction equation

HRID 1810103 reaction equation
[Cl:1][C:2]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:3]=1[CH2:4][CH2:5][NH:6][C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([O:27]C)=[O:26])=[CH:20][C:19]=1[C:29]#[N:30])[CH:13]=[CH:12]2)=[O:8].[OH-].[Na+]>CO.O.C(Cl)Cl>[C:29]([C:19]1[CH:20]=[C:21]([CH2:24][C:25]([OH:27])=[O:26])[CH:22]=[CH:23][C:18]=1[N:14]1[C:15]2[C:11](=[CH:10][C:9]([C:7](=[O:8])[NH:6][CH2:5][CH2:4][C:3]3[CH:31]=[CH:32][C:33]([Cl:35])=[CH:34][C:2]=3[Cl:1])=[CH:17][CH:16]=2)[CH:12]=[CH:13]1)#[N:30]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 68508412methyl 2-(4-(5-((2,4-dichlorophenethyl)carbamoyl)-1H-indol-1-yl)-3-cyanophenyl)acetate

Product 1

HCID 595499312-(3-Cyano-4-(5-(2,4-dichlorophenethylcarbamoyl)-1H-indol-1yl)phenyl)acetic Acid

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 2-(4-(5-((2,4-dichlorophenethyl)carbamoyl)-1H-indol-1-yl)-3-cyanophenyl)acetate in methanol (1 mL) at ambient temperature was added aqueous sodium hydroxide (5.0 N, 0.036 mL) and 5 drops of water, and the reaction was stirred for 1 hour. The reaction mixture was taken up in DCM (5 mL) and washed with 2 M HCl (5 mL). The organic layer was dried over MgSO4 and concentrated to give the desired compound as a white solid 1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 7.80 (s, 1H), 7.70 (dd, J=8.5, 2.1 Hz, 1H), 7.65 (d, J=8.6Hz, 1H), 7.57 (d, J=8.9 Hz, 1H), 7.44 (d, J=5.9 Hz, 1H), 7.32 (d, J=8.7 Hz, 1H), 7.17-7.25 (m, 3H), 6.82 (d, J=3.0 Hz, 1H), 6.24 (d, J=5.9 NH), 3.81 (s, 2H), 3.74 (q, J=6.6 Hz, 2H), 3.10 (t, J=7.0 Hz, 2H), MS(ESI)=492.3 (M+1).

Workup

  1. washwashed with 2 M HCl (5 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4bbbf96120b64809b0e665011e152fa3
Source dataset
uspto-grants-2013_01
Patent number
US08362056B2

Reaction notes

Loading…