Cesium carbonate → 4-[2-(2-Carboxy-ethyl)-3-[6-(3-methoxymethyl-5-pyrimidin-5-yl-phenoxy)-hexyl]-phenoxy]-butyric acid
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:30]=[C:31]([CH2:33][O:34][CH3:35])[CH:32]=1)[O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[C:13]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[C:14]([CH:22]=[CH:23][CH:24]=1)[O:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20].[N:36]1[CH:41]=[C:40](B(O)O)[CH:39]=[N:38][CH:37]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:27]([CH2:26][CH2:25][C:13]1[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][C:4]2[CH:3]=[C:2]([C:40]3[CH:41]=[N:36][CH:37]=[N:38][CH:39]=3)[CH:32]=[C:31]([CH2:33][O:34][CH3:35])[CH:30]=2)=[CH:24][CH:23]=[CH:22][C:14]=1[O:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])([OH:29])=[O:28]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A similar procedure as described in step 3, method B was used, starting from 4-[3-[6-(3-bromo-5-methoxymethyl-phenoxy)-hexyl]-2-(2-carboxy-ethyl)-phenoxy]-butyric acid (209 mg, 0.38 mmol), 5-pyrimidinylboronic acid (94 mg, 0.76 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (51 mg, 0.07 mmol), and cesium carbonate (492 mg, 1.51 mmol) to obtain 4-[2-(2-carboxy-ethyl)-3-[6-(3-methoxymethyl-5-pyrimidin-5-yl-phenoxy)-hexyl]-phenoxy]-butyric acid (146 mg, 70%) as a light brown paste: ES(+)-HRMS m/e calcd for C31H38N2O7 (M+H)+ 551.2752. found 551.2748.
Sources & evidence
- ORD record
- ord-d5acedebf14047e68b80dfa22e0b7782
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088936B2
Reaction notes
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