Pyridine → HCID 59425468, compound

HRID 502287Notes

Reaction equation

HRID 502287 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:25]3[CH2:28][CH2:27][CH2:26]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:11]=3)=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH:35]([O:38][C:39](Cl)=[O:40])([CH3:37])[CH3:36]>C(Cl)Cl>[CH:35]([O:38][C:39](=[O:40])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:25]3[CH2:26][CH2:27][CH2:28]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:11]=3)=[CH:4][CH:3]=1)([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 59426272HCID 59426272, compound

Product 1

HCID 59425468HCID 59425468, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(4-amino-phenyl)-1-cyclobutyl-6-morpholin-4-yl-1H-indole-3-carbonitrile (0.112 g, 0.3 mmol), pyridine (1.0 mL) in CH2Cl2 (2.0 mL) was treated with isopropylchloroformate (1.0 M in toluene, 0.6 mL, 0.6 mmol). The mixture was stirred at room temperature for 5 h and diluted with CH2Cl2 (5 mL). The organic layer was separated, washed with HCl (1.0 N, 3×2 mL), water (5 mL×2) and brine (5 mL), and purified on silica gel (CH2Cl2/EtOAc, 9:1) to provide [4-(3-cyano-1-cyclobutyl-6-morpholin-4-yl-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl ester (0.12 g, 87%).

Workup

  1. customThe organic layer was separated
  2. washwashed with HCl (1.0 N, 3×2 mL), water (5 mL×2) and brine (5 mL)
  3. custompurified on silica gel (CH2Cl2/EtOAc, 9:1)

Sources & evidence

ORD record
ord-26b5ee1477a0446dabf36905b1cba68a
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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