Nitrogen → HCID 11231903, compound

HRID 1247450Notes

Reaction equation

HRID 1247450 reaction equation
I[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:11].[O:12]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+].N#N>COCCOC.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.C(O)C>[O:12]([C:19]1[CH:20]=[CH:21][C:22]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][NH:5][C:6]3=[O:11])=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

9

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 27343774-Phenoxyphenylboronic acidHCID 21907499HCID 21907499, compound

Product 1

HCID 11231903HCID 11231903, compoundYield 52.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of Example 55A (301 mg, 1.16 mmol), 4-phenoxyphenylboronic acid (271 mg, 1.27 mmol) and Na2CO3 (403 mg, 4.75 mmol) in DME (10 mL), water (4.8 mL), and ethanol (2.4 mL) was degassed with N2 for 45 minutes, treated with Pd(PPh3)4 (120 mg), and heated to 80° C. overnight. The suspension was cooled to room temperature, poured into water, and extracted with ethyl acetate. The combined extracts were dried (Na2SO4), filtered, and concentrated. The concentrate was triturated with warm ethanol to give 183 mg of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 4.51 (s, 2H); 7.07–7.13 (m, 3H); 7.20 (t, J=7.5 Hz, 1H); 7.33 (t, J=7.1 Hz, 1H); 7.38–7.47 (m, 3H); 7.59 (t, J=7.5 Hz, 1H); 7.62–7.69 (m, 3H); 8.69 (s, 1H); MS (ESI(+)) m/e 302.1 (M+H)+.

Workup

  1. temperatureThe suspension was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was triturated with warm ethanol

Sources & evidence

ORD record
ord-0d1a262c39b647f4ab41c49cf6c94e3e
Source dataset
uspto-grants-2006_10
Patent number
US07129260B2

Reaction notes

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