HCID 52913256, compound → HCID 52913257, compound

HRID 540780Notes

Reaction equation

[CH2:1]([N:3]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[C:6](I)[C:5]([C:20]2[CH:21]=[C:22]([C:26]([NH:29][S:30]([CH2:33][C:34]([F:37])([F:36])[F:35])(=[O:32])=[O:31])([CH3:28])[CH3:27])[CH:23]=[CH:24][CH:25]=2)=[N:4]1)[CH3:2].[Cu][C:39]#[N:40]>CC(N(C)C)=O>[C:39]([C:6]1[C:5]([C:20]2[CH:21]=[C:22]([C:26]([NH:29][S:30]([CH2:33][C:34]([F:37])([F:36])[F:35])(=[O:32])=[O:31])([CH3:28])[CH3:27])[CH:23]=[CH:24][CH:25]=2)=[N:4][N:3]([CH2:1][CH3:2])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)#[N:40]

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of N-[2-(3-{1-ethyl-4-iodo-5-[4-(trifluoromethyl)phenoxy]-1H-pyrazol-3-yl}phenyl)propan-2-yl]-2,2,2-trifluoroethanesulfonamide (538 mg, 0.813 mmol), copper (I) cyanide (729 mg, 8.13 mmol) and DMA (0.813 mL) was heated to 150° C. for 16 h. The reaction was cooled, partitioned between EtOAc and sat aq NaHCO3, and filtered. The organic layer was washed with sat aq. NaHCO3 2×, dried (MgSO4) and concentrated to afford a light yellow purified twice via MPLC, 50 g silica, 10-50% EtOAc in heptanes to afford 146 mg of a white solid: MS: cal'd 561 (MH+), exp 561 (MH+).

Workup

temperatureThe reaction was cooled
custompartitioned between EtOAc
filtrationfiltered
washThe organic layer was washed with sat aq. NaHCO3 2×
dry with materialdried (MgSO4)
concentrationconcentrated
customto afford a light
customyellow purified twice via MPLC, 50 g silica, 10-50% EtOAc in heptanes

Sources & evidence

ORD record: ord-6174c0e3e32c4dce8f23d17f944b4ba6
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871796B2

Reaction notes

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