Potassium Carbonate → N-{3-[4'-(2-Allyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-yl)-2-fluoro-biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

HRID 1446097Notes

Reaction equation

HRID 1446097 reaction equation
[CH2:1]([C:4]1([C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=2)[O:8][C:7]2=[N:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][N:6]2[CH2:5]1)[CH:2]=[CH2:3].[F:22][C:23]1[CH:24]=[C:25]([N:38]2[CH2:42][CH:41]([CH2:43][NH:44][C:45](=[O:47])[CH3:46])[O:40][C:39]2=[O:48])[CH:26]=[CH:27][C:28]=1B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C.O>[CH2:1]([C:4]1([C:15]2[CH:20]=[CH:19][C:18]([C:28]3[CH:27]=[CH:26][C:25]([N:38]4[CH2:42][CH:41]([CH2:43][NH:44][C:45](=[O:47])[CH3:46])[O:40][C:39]4=[O:48])=[CH:24][C:23]=3[F:22])=[CH:17][CH:16]=2)[O:8][C:7]2=[N:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][N:6]2[CH2:5]1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22273985N-{3-[3-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamideHCID 442424052-Allyl-2-(4-bromo-phenyl)-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole

Product 1

HCID 68550437N-{3-[4'-(2-Allyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-yl)-2-fluoro-biphenyl-4-yl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

The title compound was synthesized according to the reaction scheme shown in FIG. 21. To a mixture of 2-Allyl-2-(4-bromo-phenyl)-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole (80 mg, 0.229 mmol), N-{3-[3-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (104 mg, 0.274 mmol), Pd(PPh3)4 (53 mg, 0.046 mmol) and K2CO3 (240 mg, 0.458 mmol) was added anhydrous DMF/H2O (4 mL/0.4 mL, 4.4 mL total) under N2. The reaction mixture was stirred for 2 h at 80° C., cooled to rt, quenched with water, diluted with EtOAc, washed with brine and water. The organic layers were separated, dried (MgSO4) and concentrated. Column chromatography provided 63 mg of yellow solid. 1H NMR (400 MHz, DMSO-d) δ 8.26 (t, J=5.8 Hz, 1H), 7.60 (m, 2H), 7.41 (m, 2H), 5.61 (m, 1H), 5.16 (m, 2H), 4.74 (m, 1H), 4.65 (d, J=11.2 Hz, 1H), 4.48 (d, J=11.2 Hz, 1H), 4.15 (d, J=9.0 Hz, 1H), 3.76 (m, 1H), 3.41 (d, J=1.3 Hz, 2H), 3.02 (m, 2H); ESI MS m/z 522 (M+H+)

Workup

  1. customaccording to the reaction scheme
  2. temperaturecooled to rt
  3. customquenched with water
  4. additiondiluted with EtOAc
  5. washwashed with brine and water
  6. customThe organic layers were separated
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-48d04d8ccd824378a7257426930f11d8
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

Loading…