Potassium Carbonate → HCID 68551673, compound

HRID 1446087Notes

Reaction equation

HRID 1446087 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]2[CH2:14][O:13][C:12]3=[N:15][C:16]([N+:18]([O-:20])=[O:19])=[CH:17][N:11]3[CH2:10]2)=[N:6][CH:7]=1.[F:21][C:22]1[CH:23]=[C:24]([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:25]=[C:26]([F:37])[C:27]=1B1OC(C)(C)C(C)(C)O1.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:21][C:22]1[CH:23]=[C:24]([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:25]=[C:26]([F:37])[C:27]=1[C:2]1[CH:7]=[N:6][C:5]([O:8][CH:9]2[CH2:14][O:13][C:12]3=[N:15][C:16]([N+:18]([O-:20])=[O:19])=[CH:17][N:11]3[CH2:10]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 68542912HCID 68542912, compoundHCID 68545266HCID 68545266, compound

Product 1

HCID 68551673HCID 68551673, compoundYield 43%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

To a suspension of 6-(5-bromo-pyridin-2-yloxy)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (200 mg, 0.515 mmol), N-{3-[3,5-difluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (238 mg, 0.60 mmol) (Biswajit et. al. WO 2006038100 A1 and Gravestock et. al. WO2004/078753 A1), Pd(Ph3P)4(70 mg) and K2CO3 (150 mg) in DMF/H2O (10/1.5.5 mL) was degassed. The mixture was heated to 80° C. for 2 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 (117 mg, 43%). ESI MS m/z 531.5 (M+H+). 1H NMR (400 MHz, DMSO) δ 8.30 (s, 1H), 8.28 (t, J=6.0 Hz, 1H), 8.07 (s, 1H), 7.93 (s, 1H), 7.85 (d, J=8.8 Hz, 1H), 7.46 (d, J=10.4 Hz, 1H), 7.00 (d, J=8.8 Hz, 1H), 5.77 (s, 1H), 4.80-4.68 (m, 3H), 4.48-4.40 (m, 2H), 4.14 (t, J=9.4 Hz, 1H), 3.75 (dd, J=9.2, 6.4 Hz, 1H), 3.41 (t, J=5.4 Hz, 2H), 1.82 (s, 3H).

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-b2355e5a1b4f4edcbb810bb0fe96f389
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

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