Sodium Carbonate → HCID 66893448, compound

HRID 1161985Notes

Reaction equation

HRID 1161985 reaction equation
I[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[N:14]1[CH:19]=[C:18](B(O)O)[CH:17]=[N:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[N+:11]([C:4]1[CH:3]=[C:2]([C:18]2[CH:19]=[N:14][CH:15]=[N:16][CH:17]=2)[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=1)([O-:13])=[O:12]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 21864764HCID 21864764, compound

Product 1

HCID 66893448HCID 66893448, compoundYield 898.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

Pd(PPh3)4 (240 mg, 209 mmol) was added to 7-iodo-5-nitro-1-benzofurane (1.00 g, 3.45 mmol) in DME (11 mL) and the resulting mixture was stirred for 10 min. The color went from dark red to mustard yellow. Pyrimidine-5-boronic acid (0.24 g, 0.21 mmol) and 1 M Na2CO3 (5 mL) were added and the reaction mixture was refluxed at 100° C. for 2.5 h. The mixture was concentrated in vacuo and the residue was dissolved in 1 M HCl (50 mL) and washed with diethyl ether (50 mL). The aqueous layer was made basic (pH 8), by addition of K2CO3, and extracted with chloroform (3×). The combined organic layers were dried with K2CO3, filtered and concentrated to afford 0.455 g (55%) of a yellow solid. HPLC 100%, RT: 1.870 min (System A; 10-97% over 3 min). 1H NMR (270 MHz, CDCl3) δ ppm 7.06 (d, J=2.47 Hz, 1H) 7.90 (d, J=2.23 Hz, 1H) 8.45 (d, J=2.23 Hz, 1H) 8.63 (d, J=2.23 Hz, 1H) 9.28-9.31 (m, 3H). LC-MS 242 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in 1 M HCl (50 mL)
  3. washwashed with diethyl ether (50 mL)
  4. additionby addition of K2CO3
  5. extractionextracted with chloroform (3×)
  6. dry with materialThe combined organic layers were dried with K2CO3
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5c1c970c192f4feab8899294c175df48
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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