Phenyl N-[2-(pyridin-2-ylmethyloxy)pyridin-5-yl]carbamate → 1-[2-(Pyridin-2-ylmethyloxy)pyridin-5-ylcarbamoyl]-5trifluoromethylindoline

HRID 427736Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:24])OC2C=CC=CC=2)=[CH:11][N:10]=1.[F:25][C:26]([F:37])([F:36])[C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][CH2:31][CH2:30]2>CN(C)C=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([N:32]2[C:33]3[C:29](=[CH:28][C:27]([C:26]([F:25])([F:36])[F:37])=[CH:35][CH:34]=3)[CH2:30][CH2:31]2)=[O:24])=[CH:11][N:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Phenyl N-[2-(pyridin-2-ylmethyloxy)pyridin-5-yl] carbamate (D3, 0.20 g, 0.62 mmol) in dry dimethylformamide (10 ml) was treated with 5-trifluoromethylindoline (D6, 0.12 g, 0.62 mmol) and heated at 100° C. for 1 hour. After cooling to ambient temperature, the solvent was removed in vacuo. The residue was dissolved in dichloromethane, washed with 10% aqueous sodium hydroxide solution, dried (Na2SO4) and evaporated in vacuo. The resulting oil was chromatographed on silica gel eluting with 2% methanol/dichloromethane and triturated with diethyl ether to afford the title compound (0.08 g, 31%) as an off-white solid.

Workup

temperatureAfter cooling to ambient temperature
customthe solvent was removed in vacuo
dissolutionThe residue was dissolved in dichloromethane
washwashed with 10% aqueous sodium hydroxide solution
dry with materialdried (Na2SO4)
customevaporated in vacuo
customThe resulting oil was chromatographed on silica gel eluting with 2% methanol/dichloromethane
customtriturated with diethyl ether

Sources & evidence

ORD record: ord-ca76e47d15cd479baf33ce92fcdccf81
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313145B1

Reaction notes

Loading…