Potassium Carbonate → HCID 68549761, compound

HRID 1446086Notes

Reaction equation

HRID 1446086 reaction equation
C([SiH2][O:6][C:7](C)(C)[CH:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][O:27][CH:28]4[CH2:33][O:32][C:31]5=[N:34][C:35]([N+:37]([O-:39])=[O:38])=[CH:36][N:30]5[CH2:29]4)=[CH:22][N:21]=3)=[C:16]([F:40])[CH:15]=2)[CH2:9]1)(C)(C)C.BrC1N=CC(COC2COC3=NC([N+]([O-])=O)=CN3C2)=CC=1.C([SiH2]OC(C)(C)C1OC(=O)N(C2C=CC(B3OC(C)(C)C(C)(C)O3)=C(F)C=2)C1)(C)(C)C.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:40][C:16]1[CH:15]=[C:14]([N:10]2[CH2:9][CH:8]([CH2:7][OH:6])[O:12][C:11]2=[O:13])[CH:19]=[CH:18][C:17]=1[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][O:27][CH:28]2[CH2:33][O:32][C:31]3=[N:34][C:35]([N+:37]([O-:39])=[O:38])=[CH:36][N:30]3[CH2:29]2)=[CH:22][N:21]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 75305499HCID 75305499, compoundHCID 131727901HCID 131727901, compoundHCID 131727902HCID 131727902, compound

Product 1

HCID 68549761HCID 68549761, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-{3-fluoro-4-[5-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-pyridin-2-yl]-phenyl}-oxazolidin-2-one: To a suspension of 6-(6-bromo-pyridin-3-ylmethoxy)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (150 mg, 0.40 mmol), 5-(tert-butyl-dimethyl-silanyloxymethyl)-3-[3-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-oxazolidin-2-one (198 mg, 0.44 mmol), Pd(Ph3P)4 (58 mg, 0.05 mmol) and K2CO3 (121 mg, 0.88 mmol) in DMF/H2O (10/1. 5.5 mL) was degassed. The mixture was heated to 80° C. for 2.5 h, diluted with EtOAc, washed with brine and concentrated in vacuo to give a crude product. The crude product was purified by flash chromatography (5% MeOH in EtOAc) to afford the title product (170 mg). ESI MS m/z 600.5 (M+H+).

Workup

  1. customwas degassed
  2. additiondiluted with EtOAc
  3. washwashed with brine
  4. concentrationconcentrated in vacuo
  5. customto give a crude product
  6. customThe crude product was purified by flash chromatography (5% MeOH in EtOAc)

Sources & evidence

ORD record
ord-5bca1927b3cb4934bddd09f7d97ee933
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

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