1,2-Dimethoxyethane → HCID 86634684, compound

HRID 76028Notes

Reaction equation

HRID 76028 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14](B3OC(C)(C)C(C)(C)O3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.Br[C:28]1[CH:29]=[N:30][C:31]([Cl:34])=[N:32][CH:33]=1.C([O-])([O-])=O.[Na+].[Na+].COCCOC>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]([C:11]2[CH:12]=[CH:13][C:14]([C:28]3[CH:29]=[N:30][C:31]([Cl:34])=[N:32][CH:33]=3)=[CH:15][CH:16]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 57992171Methyl 2-(trans-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclohexyl)acetate

Product 1

HCID 86634684HCID 86634684, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

PdCl2dppf (120 mg, 0.140 mmol) is added to a degassed mixture of {4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester (1.00 g, 2.79 mmol), 5-bromo-2-chloro-pyrimidine (540 mg, 2.79 mmol), 2 M Na2CO3 (2.8 mL), and DME (7.5 mL). The mixture is sealed in a glass tube and heated to 120° C. for 20 min by microwave irradiation. The reaction is diluted with EtOAc (150 mL), and the resulting suspension filtered. The filtrate is extracted with 1 N HCl (25 mL) and the organic layer dried over Na2SO4. Concentration followed by silica gel chromatography (20% EtOAc/Hexanes) affords {4-[4-(2-chloro-pyrimidin-5-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester as a white solid: 1H NMR (400 MHz, CHLOROFORM-d) δppm 1.14-1.27 (m, 2H) 1.49-1.61 (m, 2H) 1.86-1.98 (m, 5H) 2.28 (d, J=6.82 Hz, 2H) 2.56 (tt, J=12.22, 3.19 Hz, 1H) 3.70 (s, 3H) 7.37 (d, J=8.08 Hz, 2H) 7.49 (d, J=8.34 Hz, 2H) 8.81 (s, 2H); (M+H)+345.1.

Workup

  1. customThe mixture is sealed in a glass tube
  2. filtrationthe resulting suspension filtered
  3. extractionThe filtrate is extracted with 1 N HCl (25 mL)
  4. dry with materialthe organic layer dried over Na2SO4
  5. concentrationConcentration

Sources & evidence

ORD record
ord-1a6db9b35acc49c4bf99aa87e6ffa682
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

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