Cesium carbonate → 4-[2-(2-carboxy-ethyl)-3-{6-[3-(1H-indol-5-yl)-5-methoxymethyl-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].[NH:36]1[C:44]2[C:39](=[CH:40][C:41](B(O)O)=[CH:42][CH:43]=2)[CH: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:30]=[C:31]([CH2:33][O:34][CH3:35])[CH:32]=[C:2]([C:41]3[CH:40]=[C:39]4[C:44](=[CH:43][CH:42]=3)[NH:36][CH:37]=[CH:38]4)[CH:3]=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 (175 mg, 0.31 mmol), 5-indoleboronic acid (104 mg, 0.64 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (51 mg, 0.07 mmol), and cesium carbonate (417 mg, 1.28 mmol) to obtain 4-[2-(2-carboxy-ethyl)-3-{6-[3-(1H-indol-5-yl)-5-methoxymethyl-phenoxy]-hexyl}-phenoxy]-butyric acid (125 mg, 69%) as a light brown solid: ES(+)-HRMS m/e calcd for C35H41NO7 (M+Na)+ 610.2775. found 610.2774.
Sources & evidence
- ORD record
- ord-0c8f552e8cc3427fa0684e8e2e8487b7
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088936B2
Reaction notes
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