Pyridine → HCID 59424970, compound

HRID 502292Notes

Reaction equation

HRID 502292 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:22]3[CH2:25][CH2:24][CH2:23]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([S:19][CH2:20][CH3:21])[CH:11]=3)=[CH:4][CH:3]=1.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([N+]([O-])=O)=C[CH:31]=1)=[O:28].N1C=CC=CC=1.C1([C@H](O)C)CC1>CCOC(C)=O.ClCCCl>[CH:35]1([C@H:30]([O:29][C:27](=[O:28])[NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:9]([CH:22]4[CH2:23][CH2:24][CH2:25]4)[C:10]4[C:15]([C:16]=3[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([S:19][CH2:20][CH3:21])[CH:11]=4)=[CH:6][CH:7]=2)[CH3:31])[CH2:34][CH2:33]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 6999829(1R)-1-cyclopropylethan-1-olHCID 59425515HCID 59425515, compound

Product 1

HCID 59424970HCID 59424970, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To 2-(4-amino-phenyl)-1-cyclobutyl-6-ethylsulfanyl-1H-indole-3-carbonitrile (230.0 mg, 0.66 mmol) was combined with p-nitrophenyl chloroformate (266 mg, 1.32 mmol), DCE (3.0 mL), and pyridine (104.7 mg, 1.32 mmol) and stirred at room temperature for 2 h. (R)-1-Cyclopropylethanol (115.0, 1.34 mmol) was added and mixture was heated at 80° C. for 2 h. The reaction mixture was diluted with EtOAc and washed with sat. aq. K2CO3 (2×15 mL), water, and brine. The organic layer was dried, concentrated and purified on silica gel (EtOAc/hexane 10%)) to provide (R)-[4-(3-cyano-1-cyclobutyl-6-ethylsulfanyl-1H-indol-2-yl)-phenyl]-carbamic acid 1-cyclopropyl-ethyl ester (209 mg, 69%) as a white solid.

Workup

  1. additionwas added
  2. washwashed with sat. aq. K2CO3 (2×15 mL), water, and brine
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. custompurified on silica gel (EtOAc/hexane 10%))

Sources & evidence

ORD record
ord-55cda0b19c2b4d76bdb01fa2b8902a3a
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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