Cesium carbonate → 4-[2-(2-Carboxy-ethyl)-3-[6-(3',4'-difluoro-5-methoxymethyl-biphenyl-3-yloxy)-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].[F:36][C:37]1[CH:38]=[C:39](B(O)O)[CH:40]=[CH:41][C:42]=1[F:43].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:39]=[CH:38][C:37]([F:36])=[C:42]([F:43])[CH:41]=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 (184 mg, 0.33 mmol), 3,4-difluorophenylboronic acid (106 mg, 0.66 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (44 mg, 0.06 mmol), and cesium carbonate (434 mg, 1.33 mmol) to obtain 4-[2-(2-carboxy-ethyl)-3-[6-(3′,4′-difluoro-5-methoxymethyl-biphenyl-3-yloxy)-hexyl]-phenoxy]-butyric acid (180 mg, 93%) as a light yellow paste: ES(+)-HRMS m/e calcd for C33H38F2O7 (M+Na)+ 607.2478. found 607.2478.
Sources & evidence
- ORD record
- ord-e634d2e59ade458a80975041103da02e
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088936B2
Reaction notes
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