Water → HCID 68427754, compound

HRID 502261Notes

Reaction equation

HRID 502261 reaction equation
[CH:1]([O:4][C:5](=[O:29])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([CH:25]3[CH2:28][CH2:27][CH2:26]3)[C:15]3[C:20]([C:21]=2[C:22]#[N:23])=[CH:19][CH:18]=[C:17]([OH:24])[CH:16]=3)=[CH:9][CH:8]=1)([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].CC1(C)[O:41][CH:40]([CH2:42][CH2:43]OS(C2C=CC([N+]([O-])=O)=CC=2)(=O)=O)[CH2:39][O:38]1.O>CN(C=O)C>[CH:1]([O:4][C:5](=[O:29])[NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]([CH:25]3[CH2:28][CH2:27][CH2:26]3)[C:15]3[C:20]([C:21]=2[C:22]#[N:23])=[CH:19][CH:18]=[C:17]([O:24][CH2:43][CH2:42][CH:40]([OH:41])[CH2:39][OH:38])[CH:16]=3)=[CH:11][CH:12]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 59425079HCID 59425079, compoundHCID 86617165HCID 86617165, compound

Product 1

HCID 68427754HCID 68427754, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of [4-(3-cyano-1-cyclobutyl-6-hydroxy-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl ester (100 mg, 0.26 mmol) in DMF (3 mL) is added K2CO3 (43.2 mg, 0.312 mmole) and 4-nitrobenzenesulfonic acid 2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester (129 mg, 0.39 mmole) and the reaction is stirred for 18 h at ambient temperature. The reaction mixture is then poured into cold water and the precipitate is collected by filtration and washed with EtOAc/hexane and dried in vacuo to afford 96 mg, 84% of the desired product, (4-{3-cyano-1-cyclobutyl-6-[2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-1H-indol-2-yl}carbamic acid isopropyl ester, compound 1428.

Workup

  1. filtrationthe precipitate is collected by filtration
  2. washwashed with EtOAc/hexane
  3. customdried in vacuo

Sources & evidence

ORD record
ord-c369f9721ec746b2926aa18937f56786
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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