Isopropyl chloroformate → HCID 49772362, compound

HRID 252599Notes

Reaction equation

HRID 252599 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:21]3[CH2:23][CH2:22]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[CH:11]=3)=[CH:4][CH:3]=1.[CH:24]([O:27][C:28](Cl)=[O:29])([CH3:26])[CH3:25]>N1C=CC=CC=1.C1(C)C=CC=CC=1.O>[CH:24]([O:27][C:28](=[O:29])[NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH:21]3[CH2:23][CH2:22]3)[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[CH:11]=3)=[CH:6][CH:7]=1)([CH3:26])[CH3:25]

Participants

6

Reactant 2

HCID 7917Isopropyl chloroformateHCID 59425315HCID 59425315, compound

Product 1

HCID 49772362HCID 49772362, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

To a solution of the compound obtained in step E (61 mg, 0.2 mmol) in dry pyridine (2.0 mL) is added isopropylchloroformate (0.3 mL, 1.0 M, 0.3 mmol) in toluene. The mixture is stirred at room temperature overnight and diluted with water (10 mL). The organic layer is extracted with DCM (10 mL) and washed with HCl (2N, 2×3 mL), water (2×4 mL) and brine (3 mL) and chromatographed (silica gel, EtOAc/DCM, 0.5/9.5) to provide the product, [4-(3-cyano-1-cyclopropyl-6-methoxyindol-2-yl)phenyl]carbamic acid isopropyl ester (66 mg, 85%).

Workup

  1. extractionThe organic layer is extracted with DCM (10 mL)
  2. washwashed with HCl (2N, 2×3 mL), water (2×4 mL) and brine (3 mL)
  3. customchromatographed (silica gel, EtOAc/DCM, 0.5/9.5)

Sources & evidence

ORD record
ord-bdca4f7df5894d65bca3c55c3a552ef3
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

Loading…