4-(Trifluoromethyl)phenyl isocyanate → HCID 49865951, compound

HRID 2063460Notes

Reaction equation

[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1)=[C:2]=[O:3].OC(C(F)(F)F)=O.[Cl:21][C:22]1[CH:39]=[CH:38][C:25]([CH2:26][N:27]2[C:31]([C@H:32]3[CH2:36][CH2:35][CH2:34][NH:33]3)=[N:30][N:29]=[C:28]2[CH3:37])=[CH:24][CH:23]=1.C(N(CC)C(C)C)(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.[Cl-].[Na+].O>[Cl:21][C:22]1[CH:39]=[CH:38][C:25]([CH2:26][N:27]2[C:28]([CH3:37])=[N:29][N:30]=[C:31]2[C@H:32]2[CH2:36][CH2:35][CH2:34][N:33]2[C:2]([NH:1][C:4]2[CH:5]=[CH:6][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:8][CH:9]=2)=[O:3])=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirring solution of 1-isocyanato-4-(trifluoromethyl)benzene (48.6 mg, 0.26 mmol) in 8 mL of CH2Cl2 at 0° C. was slowly added a solution of the (R)-4-(4-chlorobenzyl)-3-methyl-5-(pyrrolidin-2-yl)-4H-1,2,4-triazole TFA salt (0.1237 g, 0.2 mmol) and N,N-diisopropylethylamine (0.108 mL, 0.620 mmol) in dichloromethane (2 mL). The resulting mixture was stirred 0° C. for 30 minutes, then at room temperature overnight. The reaction mixture was treated with sat. aqueous NaHCO3 (10 mL) and brine, dried over Na2SO4, and concentrated in vacuo. Flash chromatography purification (Hex/EtOAc gradient, 10-100% EtOAc with 10% of MeOH) afforded the desired product (49.2 mg, 53.0%).

Workup

customat room temperature
customovernight
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customFlash chromatography purification (Hex/EtOAc gradient, 10-100% EtOAc with 10% of MeOH)

Sources & evidence

ORD record: ord-3164573ebc894f818180917181ba7a98
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288371B2

Reaction notes

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