Ethyl Acetate → HCID 66611289, compound

HRID 1465202Notes

Reaction equation

[F:1][C:2]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([OH:17])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[C:31]([O:35][C:36](=[O:42])[NH:37][CH2:38][CH2:39][CH2:40]Br)([CH3:34])([CH3:33])[CH3:32].CCOC(C)=O>CN(C=O)C>[F:1][C:2]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH2:40][CH2:39][CH2:38][NH:37][C:36](=[O:42])[O:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-(2-fluoro-4-nitro-phenoxy)-6-methoxy-quinolin-7-ol (511 mg, 1.55 mmol, 1.0 eq.) and potassium carbonate (428 mg, 3.1 mmol, 2.0 eq.) in dry DMF (10 mL) was added tert-butyl(3-bromopropyl)carbamate (480 mg, 2.01 mmol, 1.3 eq.). The mixture was stirred for 3 h at 90° C. and then cooled to RT. EtOAc was added and the organic phase was washed three times with water. The organic phase was dried over MgSO4 and solvents were removed in vacuo. The desired product R1 was obtained as brown oil and was used without further purification in the next step. MS (ES) C24H26FN3O7 requires: 487. Found: 488 (M+H)+.

Workup

temperaturecooled to RT
washthe organic phase was washed three times with water
dry with materialThe organic phase was dried over MgSO4 and solvents
customwere removed in vacuo
customwas obtained as brown oil
customwas used without further purification in the next step

Sources & evidence

ORD record: ord-bf8efb09a1694d619518f60576ebb292
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999982B2

Reaction notes

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