Potassium Carbonate → HCID 68546653, compound

HRID 1446067Notes

Reaction equation

HRID 1446067 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[N:16]3)[O:11][C:10]2=[O:20])[CH:5]=[CH:6][C:7]=1I.[N+:21]([C:24]1[N:25]=[C:26]2[N:31]([CH:32]=1)[CH2:30][C@H:29]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38](B3OC(C)(C)C(C)(C)O3)=[CH:37][N:36]=1)[CH2:28][O:27]2)([O-:23])=[O:22].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.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>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@@H:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[N:16]3)[O:11][C:10]2=[O:20])[CH:5]=[CH:6][C:7]=1[C:38]1[CH:37]=[N:36][C:35]([CH2:34][O:33][C@H:29]2[CH2:28][O:27][C:26]3=[N:25][C:24]([N+:21]([O-:23])=[O:22])=[CH:32][N:31]3[CH2:30]2)=[CH:40][CH:39]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 11257720(R)-5-((1H-1,2,3-Triazol-1-yl)methyl)-3-(3-fluoro-4-iodophenyl)oxazolidin-2-oneHCID 68548991HCID 68548991, compound

Product 1

HCID 68546653HCID 68546653, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

3-(3-Fluoro-4-iodo-phenyl)-5(R)-[1,2,3]triazol-1-ylmethyl-oxazolidin-2-one (90 mg, 0.232 mmol), 2-Nitro-6(S)-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ylmethoxy]-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (108 mg, 0.278 mmol), K2CO3 (244 mg, 0.464 mmol) and Pd(PPh3)4 (27 mg, 0.023 mmol) were combined and suspended in DMF (2 ml) and water (0.2 ml). The mixture was heated to 60° C. for 1½ hours then quenched with sat. aqueous NH4Cl (2 mL) at rt. The mixture was diluted with EtOAc (10 mL) and washed with water (5 mL×5). The organic phases were dried (MgSO4) and concentrated. Column chromatography (2% MeOH/CH2Cl2) provided 60 mg (50%) of the title product as yellow solid. LCMS (ESI) m/z 523 (M+H+).

Workup

  1. customthen quenched with sat. aqueous NH4Cl (2 mL) at rt
  2. additionThe mixture was diluted with EtOAc (10 mL)
  3. washwashed with water (5 mL×5)
  4. dry with materialThe organic phases were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-829e50a7cb494ac99901704349a206ea
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

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