Pyridine → HCID 131727378, compound

HRID 1788446Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:43]=[CH:42][C:8]2[N:9]([CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)[C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[C:17]([C:22]3[C:27]([C:28]5[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=5)=[CH:26][CH:25]=[C:24]([OH:35])[CH:23]=3)[CH:16]=[CH:15]4)=[N:11][C:7]=2[CH:6]=1)=[O:4].N1C=CC=CC=1.[O:50](S(C(F)(F)F)(=O)=O)[S:51]([C:54]([F:57])([F:56])[F:55])(=O)=[O:52]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]([C:5]1[CH:43]=[CH:42][C:8]2[N:9]([CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)[C:10]([C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[C:17]([C:22]3[C:27]([C:28]5[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=5)=[CH:26][CH:25]=[C:24]([O:35][S:51]([C:54]([F:57])([F:56])[F:55])(=[O:52])=[O:50])[CH:23]=3)[CH:16]=[CH:15]4)=[N:11][C:7]=2[CH:6]=1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1 g (1.7 mmol) of Compound 475a in 20 mL of DCM, 550 μL (6.8 mmol) of pyridine, and 21 mg (0.17 mmol) of DMAP were added and the entire mixture was cooled to 0° C. Dropwise, 860 μL of Tf2O was added. The reaction was then stirred at room temperature for 1 h. Finally the reaction mixture was evaporated, and the product dissolved in ethyl acetate, washed with cold water (2×), brine (2×), dried with Na2SO4 and evaporated again to give the title intermediate as a white solid foam in quantitative yield.

Workup

customFinally the reaction mixture was evaporated
dissolutionthe product dissolved in ethyl acetate
washwashed with cold water (2×), brine (2×)
dry with materialdried with Na2SO4
customevaporated again

Sources & evidence

ORD record: ord-836801a6af724cc5b6f5ef38e88bef22
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511145B2

Reaction notes

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