Sodium Carbonate → HCID 67328563, compound

HRID 221411Notes

Reaction equation

HRID 221411 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]([CH3:21])[CH3:20])[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:22]1[CH:27]=[C:26](B(O)O)[CH:25]=[N:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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]>[CH3:20][N:19]([CH2:18][C:14]1[CH:13]=[C:12]([NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([C:23]3[N:24]=[CH:25][CH:26]=[CH:27][N:22]=3)=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH:17]=[CH:16][CH:15]=1)[CH3:21]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 61216416HCID 61216416, compound

Product 1

HCID 67328563HCID 67328563, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Bromo-N-(3-((dimethylamino)methyl)phenyl)benzenesulfonamide (273 mg, 0.74 mmol), pyrimidine-5-boronic acid (101 mg, 0.81 mmol) and Pd(dppf)Cl2 (29 mg, 5 mol %) were dissolved in DME (4 mL) and 2M Na2CO3 solution (1.11 mL, 2.22 mmol) was added. The vessel was sealed and purged with argon for 5 minutes while it was placed in an ultrasonic bath. The flask was then placed in a pre-heated oil bath (90° C.) for 1 hour. After this time the reaction was cooled to room temperature and absorbed onto silica. The material was semi-purified by flash chromatography (Isolute II, 70 g silica cartridge, SP4) eluting with 4.5-5.5% MeOH/NH3:DCM, followed by reverse-phase HPLC and finally by trituration from 1:1 v/v Et2O:hexane to give the title compound as a colourless solid (26 mg, 10%). 1H NMR (300 MHz, DMSO-d6): δ 2.13 (6H, s), 3.32 (2H, s), 6.99 (1H, br s), 7.06 (2H, d, J=9 Hz), 7.21 (1H, t, J=8 Hz), 7.62 (2H, d, J=8.5 Hz), 7.89 (2H, d, J=8.5 Hz), 8.92 (2H, s) and 9.25 (1H, s). LCMS: (MH)+=369; (M−H)−=367.

Workup

  1. customThe vessel was sealed
  2. custompurged with argon for 5 minutes while it
  3. customwas placed in an ultrasonic bath
  4. customThe flask was then placed in a pre-heated oil bath
  5. customabsorbed onto silica
  6. washeluting with 4.5-5.5% MeOH/NH3

Sources & evidence

ORD record
ord-1c1666f3d6e54406ac6525f58e9445e6
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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