Sodium hydride → HCID 57808168, compound

HRID 730315Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:15]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:18]=[CH:17][N:16]=1>CN(C=O)C>[F:30][C:27]([F:28])([F:29])[C:24]1[CH:23]=[CH:22][C:21]([C:19]2[CH:20]=[CH:15][N:16]=[C:17]([O:1][C:2]3[CH:11]=[C:10]4[C:5]([CH:6]=[CH:7][CH:8]=[N:9]4)=[CH:4][CH:3]=3)[CH:18]=2)=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 155 °C

Procedure

To an oven-dried, 50-mL, round-bottomed flask were added 7-hydroxyquinoline (Aldrich) (87 mg, 0.6 mmol) and DMF (1 mL). The solution was place under nitrogen, and NaH (24 mg, 0.6 mmol) was added in one portion. After stirring for 10 min, 2-chloro-4-(4-trifluoromethylphenyl) pyridine (Example 410 (c), 129 mg, 0.5 mmol) was added. The reaction mixture was heated in a 155° C. oil bath for 72 h. After cooling to room temperature, the reaction mixture was partitioned between EtOAc and brine. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4, concentrated in vacuo. The crude material was purified on a Biotage 40 S column (3:1 hexanes:EtOAc) to give the title compound as an off-white solid. MS (ESI, pos. ion) m/z: 367 (M+1). Mp: 156.5-158.5° C.

Workup

temperatureAfter cooling to room temperature
customthe reaction mixture was partitioned between EtOAc and brine
extractionThe aqueous layer was extracted with EtOAc
dry with materialthe combined organic layers were dried over Na2SO4
concentrationconcentrated in vacuo
customThe crude material was purified on a Biotage 40 S column (3:1 hexanes:EtOAc)

Sources & evidence

ORD record: ord-3d611c09c1ea4d0fa4d46beb656e165e
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582657B2

Reaction notes

Loading…