Sodium Carbonate → HCID 89813741, compound

HRID 525402Notes

Reaction equation

HRID 525402 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[C@@H:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:17]([CH3:26])([CH3:25])[O:16][C:15]3=[O:27])=[CH:10][CH:9]=2)=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[CH:4][N:3]=1.Cl[C:38]1[N:43]=[C:42]([C:44]#[N:45])[CH:41]=[CH:40][N:39]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:25][C:17]1([CH3:26])[O:16][C:15](=[O:27])[N:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]3[CH:6]=[C:5]([C:38]4[N:43]=[C:42]([C:44]#[N:45])[CH:41]=[CH:40][N:39]=4)[CH:4]=[N:3][C:2]=3[F:1])=[CH:9][CH:10]=2)[C@H:18]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2466472-Chloropyrimidine-4-carbonitrileHCID 89815465HCID 89815465, compound

Product 1

HCID 89813741HCID 89813741, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A microwave vial was charged with (S)-3-(4-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (0.074 g, 0.152 mmol), 2-chloropyrimidine-4-carbonitrile (commercially available from Synthonix, Wake Forest, N.C.)(0.023 g, 0.167 mmol), sodium carbonate (0.048 g, 0.455 mmol), dioxane (2.0 mL), and water (0.400 mL). Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) DCM adduct (0.012 g, 0.015 mmol) was added, the system was purged with argon, and the tube was sealed. The mixture was then stirred at 100° C. in a microwave for 1 hour. The resulting reaction mixture was filtered through Celite® brand filter aid and the filtrate was concentrated to afford a brown solid. The resulting solid was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-50% EtOAc-hexane) to afford (S)-2-(5-(4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)phenyl)-6-fluoropyridin-3-yl)pyrimidine-4-carbonitrile (0.051 g, 0.110 mmol, 72.3% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.93 (s, 3H), 1.66 (s, 3H), 5.53 (s, 1H), 7.14-7.50 (m, 5H), 7.59-7.78 (m, 4H), 8.17 (d, J=4.99 Hz, 1H), 8.78 (dd, J=9.68, 2.35 Hz, 1H), 9.09 (dd, J=2.30, 0.93 Hz, 1H), 9.29 (d, J=4.89 Hz, 1H). m/z (ESI) 466 (M+H)+.

Workup

  1. customthe system was purged with argon
  2. customthe tube was sealed
  3. customThe resulting reaction mixture
  4. filtrationwas filtered through Celite® brand
  5. filtrationfilter aid
  6. concentrationthe filtrate was concentrated
  7. customto afford a brown solid
  8. customThe resulting solid was purified

Sources & evidence

ORD record
ord-5fb90f390dbe4cf18ce1b5554e28b56f
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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