Sodium Carbonate → (4-{4-[2-(3-Fluorophenylamino)-pyrimidin-5-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

HRID 76026Notes

Reaction equation

HRID 76026 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)=[N:6][CH:7]=1.[CH3:16][O:17][C:18](=[O:41])[CH2:19][CH:20]1[CH2:25][CH2:24][CH:23]([C:26]2[CH:31]=[CH:30][C:29](B3OC(C)(C)C(C)(C)O3)=[CH:28][CH:27]=2)[CH2:22][CH2:21]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[CH3:16][O:17][C:18](=[O:41])[CH2:19][CH:20]1[CH2:21][CH2:22][CH:23]([C:26]2[CH:27]=[CH:28][C:29]([C:2]3[CH:3]=[N:4][C:5]([NH:8][C:9]4[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=4)=[N:6][CH:7]=3)=[CH:30][CH:31]=2)[CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 57992171Methyl 2-(trans-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclohexyl)acetateHCID 63874387HCID 63874387, compound

Product 1

HCID 66615836(4-{4-[2-(3-Fluorophenylamino)-pyrimidin-5-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
125 °C

Procedure

The mixture of (5-bromopyrimidin-2-yl)-(3-fluorophenyl)-amine (75 mg, 0.28 mmol), {4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester (Patent WO2004 047755) (100 mg, 0.28 mmol), PdCl2dppf (12 mg, 0.014 mmol), sodium carbonate (2M solution, 0.35 mL) and DME (2 mL) is heated in a microwave at 125° C. for 15 min. The reaction mixture is extracted with EtOAc, washed with NH4Cl solution. The organic phase is dried with MgSO4, filtered and it is used directly in the next step: (M+H)+420.3.

Workup

  1. extractionThe reaction mixture is extracted with EtOAc
  2. washwashed with NH4Cl solution
  3. dry with materialThe organic phase is dried with MgSO4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-fb8c687d68c842da8c05ad1306d53884
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

Loading…