Cesium carbonate → HCID 73292340, compound

HRID 1749009Notes

Reaction equation

HRID 1749009 reaction equation
[C:1](=[O:4])([O-])[O-].[Cs+].[Cs+].[CH2:7]1[CH2:17][CH2:16][N:15]2[C:10](=[N:11][CH2:12][CH2:13][CH2:14]2)[CH2:9][CH2:8]1.[C:18]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)([O:20][CH3:21])=[O:19]>CN(C=O)C.CC(=O)OCC.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd]>[CH2:9]([C:10]1[N:15]([CH2:16][CH2:17][C:7]2[CH:16]=[CH:17][CH:7]=[CH:8][CH:9]=2)[C:1](=[O:4])[C:13]2[C:12](=[C:12]([C:25]3[CH:26]=[CH:27][C:22]([C:18]([O:20][CH3:21])=[O:19])=[CH:23][CH:24]=3)[CH:13]=[CH:14][CH:14]=2)[N:11]=1)[CH3:8]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27343694-Methoxycarbonylphenylboronic acid

Product 1

HCID 73292340HCID 73292340, compoundYield 1,038.4%

Reagents, catalysts & solvents 3

HCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The white crystal (3.7 g, 11.83 mmol) from step 1 mixed with Herrmann's palladacycle (0.166 g, 0.18 mmol), [(t-Bu)PH]BF4(0.206 g, 0.71 mmol), cesium carbonate (3.87 g, 11.82 mmol), and DBU (0.18 mL, 1.20 mmol) in DMF (30 mL) under Ar was added with 4-(carbomethoxy)phenylboronic acid (2.17 g, 11.82 mmol). The reaction mixture was irradiated with microwave 120 W to reflux for 20 min. After irradiation, the resulting mixture was evaporated to get oil residue. The residue suspended in EA (50 mL) was washed with water (3×50 mL). The EA layer dried over MgSO4 was evaporated to give title compound as beige solid (2.57 g, 52.7%). Rf=0.11 (EA/Hexane=1:4); 1H NMR (400 MHz, CDCl3) δ 1.14 (t, J=7.2 Hz, 3H), 2.62 (q, J=7.2 Hz, 2H), 2.97 (dd, J=7.6 Hz, 2H), 4.23 (dd, J=7.6 Hz, 2H), 7.18-7.27 (m, 5H), 7.45 (t, J=7.6 Hz, 1H), 7.69-7.71 (m, 2H), 7.74 (dd, J=7.6 and 1.2 Hz, 1H), 8.03-8.05 (m, 2H), 8.28 (dd, J=8.0 and 1.6 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 10.7, 28.0, 34.7, 45.3, 52.1, 121.2, 126.2, 126.9 (2C), 127.2, 128.7, 128.83, 128.85, 128.9, 130.2, 130.7, 134.8, 137.5, 138.0, 143.2, 144.3, 156.4, 162.3, 167.2;

Workup

  1. customThe reaction mixture was irradiated with microwave 120 W
  2. temperatureto reflux for 20 min
  3. customAfter irradiation
  4. customthe resulting mixture was evaporated
  5. customto get oil residue
  6. washwas washed with water (3×50 mL)
  7. dry with materialThe EA layer dried over MgSO4
  8. customwas evaporated

Sources & evidence

ORD record
ord-832f42fb530a4df7bd2b72281e8743cb
Source dataset
uspto-grants-2015_10
Patent number
US09155739B2

Reaction notes

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