3-(Trifluoromethyl)phenyl isocyanate → HCID 59596360, compound

HRID 2264597Notes

Reaction equation

HRID 2264597 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1.[NH2:14][C:15]1[N:20]=[C:19]([O:21][C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][CH2:26][CH2:25]3)[CH:18]=[C:17]([Cl:31])[N:16]=1>C1COCC1.CCOC(C)=O.O>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:27]2[C:28]3[C:24](=[CH:23][C:22]([O:21][C:19]4[CH:18]=[C:17]([Cl:31])[N:16]=[C:15]([NH2:14])[N:20]=4)=[CH:30][CH:29]=3)[CH2:25][CH2:26]2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 87433923HCID 87433923, compound

Product 1

HCID 59596360HCID 59596360, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 226 mg (1.21 mMol) 3-trifluoromethyl-phenylisocyanat in 5 ml THF is added dropwise to 302 mg (1.15 mMol) 5-(2-amino-6-chloro-pyrimidin-4-yloxy)-2,3-dihydro-indole (Step 24.2) in 5 ml THF. After 30 min, the reaction mixture is diluted with EtOAc and water, the aqueous layer separated off and extracted twice with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; EtOAc/hexane 1:4→2:5) gives the title compound: MS: [M+1]+=450; TLC(hexane/EtOAc 3:2): Rf=0.08; HPLC: AtRet=15.6.

Workup

  1. customthe aqueous layer separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic phases are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e69599f1320a43bebc448d29878d7319
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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