Sodium Carbonate → HCID 86588597, compound

HRID 1830977Notes

Reaction equation

HRID 1830977 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12]([O:14][CH2:15][C:16]([Cl:19])([Cl:18])[Cl:17])=[O:13])[CH2:10][CH:9]3[CH2:20][CH2:21][CH2:22][N:8]3[C:7](=[O:23])[C:6]=2[CH:24]=1.[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC=CC=1.O.C(O)C.C(OCC)(=O)C.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:25]1([C:2]2[CH:3]=[CH:4][C:5]3[N:11]([C:12]([O:14][CH2:15][C:16]([Cl:18])([Cl:19])[Cl:17])=[O:13])[CH2:10][CH:9]4[CH2:20][CH2:21][CH2:22][N:8]4[C:7](=[O:23])[C:6]=3[CH:24]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

9

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 22046637HCID 22046637, compound

Product 1

HCID 86588597HCID 86588597, compoundYield 95%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 134 (0.5 g, 1.0 mmol), benzeneboronic acid (0.15 g, 1.22 mmol), Pd(PPh3)4 and anhydrous Na2CO3 (0.16 g, 1.48 mmol) in distilled benzene (20 mL), water (2 ml) and ethanol (2 mL) was heated at reflux overnight. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water (2×20 mL). The organic phase was dried over MgSO4 and evaporated to yield a crude yellow oil. Purification by flash chromatography (ethyl acetate/petroleum ether 30/70 to 70/30) furnished the title compound (0.43 g, 95%): 1H NMR (270 MHz, CDCl3) δ1.98-2.09 (m, 2H); 2.12-2.15 (m, 2H); 3.51-3.62 (m, 2H); 3.7-3.79 (m, 1H); 4.28 (d, J=12.1 Hz, 1H); 4.73 (d, J=4.4 Hz, 1H); 5.18 (d, J=12.1 Hz, 1H); 5.66-5.73 (dd, J=4.8, J=9.8 Hz, 1H); 7.33-7.48 (m, 4H); 7.61-7.70 (m, 3H); 8.02 (d, J=2.2 Hz, 1H). 13C NMR (CDCl3) δ22.9, 28.7, 46.4; 59.8; 75.0; 77.3; 86.0; 94.9; 127.0; 127.3; 128.0; 128.9; 129.6; 130.8; 132.9; 133.5; 139.2; 141.1; 154.4; 166.9. MS: m/e (relative intensity) 468 (M+., 10), 292 (25), 222 (100), 195 (10), 166 (35), 140 (10), 70 (70). HRMS Calculated for C21H19C13N2O4: 468.0411. Found: 468.0410. [α]25D=+103.80 (c=0.42, CHCl3).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. washwashed with water (2×20 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated
  6. customto yield a crude yellow oil
  7. customPurification by flash chromatography (ethyl acetate/petroleum ether 30/70 to 70/30)

Sources & evidence

ORD record
ord-5f4c7474a5c44b0f910fa1f98bda2567
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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