Triethylamine → HCID 49772202, compound

HRID 1009645Notes

Reaction equation

HRID 1009645 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:23][CH3:24])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH:20]([F:22])[F:21])[CH:11]=3)=[CH:4][CH:3]=1.[CH2:25]([N:28]=[C:29]=[O:30])[CH2:26][CH3:27].C(N(CC)CC)C>ClCCCl>[C:17]([C:16]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH:20]([F:22])[F:21])=[CH:13][CH:14]=2)[N:9]([CH2:23][CH3:24])[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:29]([NH:28][CH2:25][CH2:26][CH3:27])=[O:30])=[CH:3][CH:4]=1)#[N:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61033Propyl isocyanateHCID 25051495HCID 25051495, compound

Product 1

HCID 49772202HCID 49772202, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2-(4-aminophenyl)-6-difluoromethoxy-1-ethyl-1H-indole-3-carbonitrile (200 mg, 0.611 mmol) in 1,2-dichloroethane (2 mL) is treated with n-propylisocyanate (115 mL, 1.23 mmol) and triethylamine (170 mL, 1.22 mmol). The resulting solution is stirred at ambient temperature for 12 hours, and then concentrated. The residual material is separated by silica gel chromatography (1/2 ethyl acetate-hexane) to afford the title product as a solid.

Workup

  1. concentrationconcentrated
  2. customThe residual material is separated by silica gel chromatography (1/2 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-4f53370d0f484ef99dffa8e4c0ddde32
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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