Water → isopropyl-methyl-carbamic acid 4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl ester

HRID 502246Notes

Reaction equation

HRID 502246 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1C1C=CC(O)=CC=1)[CH3:2].Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][C:30]([N+]([O-])=O)=[CH:29][CH:28]=1)=[O:25].[CH:36]([NH:39][CH3:40])([CH3:38])[CH3:37].O>CCN(CC)CC.C(Cl)Cl.C(OCC)(=O)C>[C:14]([C:5]1[C:6]2[C:11](=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[N:3]([CH2:1][CH3:2])[C:4]=1[C:30]1[CH:31]=[CH:32][C:27]([O:26][C:24](=[O:25])[N:39]([CH:36]([CH3:38])[CH3:37])[CH3:40])=[CH:28][CH:29]=1)#[N:15]

Participants

8

Reactant 4

HCID 962WaterHCID 78485N-MethylisopropylamineHCID 821294-Nitrophenyl chloroformateHCID 594253351-ethyl-2-(4-hydroxyphenyl)-6-methoxy-1H-indole-3-carbonitrile

Product 1

HCID 59425594isopropyl-methyl-carbamic acid 4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl esterYield 70%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-ethyl-2-(4-hydroxyphenyl)-6-methoxy-1H-indole-3-carbonitrile (58 mg, 0.2 mmol) in 4 mL of Et3N and CH2Cl2 (1/1) is added p-nitrophenyl chloroformate (100 mg, 0.5 mmol) at room temperature. After the mixture is stirred for about 1 h, N-isopropylmethylamine (0.062 mL, 0.6 mmol) is added. The mixture is stirred for 3 h and then water and ethyl acetate are added to the reaction mixture. The organic layer is separated, washed with aqueous HCl (1N) and brine, dried over anhydrous Na2SO4, and filtered and concentrated. The crude solid is purified by preparative HPLC to afford 70% of isopropyl-methyl-carbamic acid 4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl ester.

Workup

  1. stirringThe mixture is stirred for 3 h
  2. customThe organic layer is separated
  3. washwashed with aqueous HCl (1N) and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude solid is purified by preparative HPLC

Sources & evidence

ORD record
ord-7427fe0c2a6f404ab1afc8a7ad10eba2
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

Loading…