Methane → (S)-methyl 1-(1,3-benzodioxol-5-yl)-3-[4-methoxy-2-[2-(phenylmethoxy)ethoxy]phenyl]-5-propoxy-1H-indene-2-carboxylate

HRID 277498Notes

Reaction equation

HRID 277498 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@H:10]3[C:18]4[C:13](=[CH:14][C:15]([O:19][CH2:20][CH2:21][CH3:22])=[CH:16][CH:17]=4)[C:12](OS(F)(=O)=O)=[C:11]3[C:28]([O:30][CH3:31])=[O:29])=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[C:36]([O:43][CH2:44][CH2:45][O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:35]=1.C([O-])([O-])=O.[K+].[K+].C>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].CCO.C1(C)C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@H:10]3[C:18]4[C:13](=[CH:14][C:15]([O:19][CH2:20][CH2:21][CH3:22])=[CH:16][CH:17]=4)[C:12]([C:37]4[CH:38]=[CH:39][C:34]([O:33][CH3:32])=[CH:35][C:36]=4[O:43][CH2:44][CH2:45][O:46][CH2:47][C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)=[C:11]3[C:28]([O:30][CH3:31])=[O:29])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

8

Reactant 4

HCID 297Methane2×HCID 11430Potassium CarbonateHCID 11123220(S)-Methyl-1-(1,3-benzodioxol-5-yl)-3-[(fluorosulfonyl)oxy]5-propoxy-1H-indene-2-carboxylateHCID 18314635(4-Methoxy-2-[2-(phenylmethoxy)ethoxy]phenyl]boronic acid2×

Product 1

HCID 12971682(S)-methyl 1-(1,3-benzodioxol-5-yl)-3-[4-methoxy-2-[2-(phenylmethoxy)ethoxy]phenyl]-5-propoxy-1H-indene-2-carboxylateYield 98.3%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A 50 mL three-necked flask under nitrogen was charged with (S)-methyl 1-(1,3-benzodioxol-5-yl)-3-[(fluorosulfonyl)oxy]-5-propoxy-1H-indene-2-carboxylate (prepared as described in Example 1 (vii)) (500 mg, 1.07 mmol), (4-methoxy-2-[2-(phenylmethoxy)ethoxy]phenyl]boronic acid (Compound (v)) (330 mg, 1.09 mmol), toluene (15 mL), EtOH (1 mL), and Pd(dppf)Cl2 catalyst (24 mg, 0.033 mmol). The mixture was stirred for 0.5 h at room temperature followed by the addition of 1.3 M K2CO3 solution (1.0 mL, 1.3 mmol) and heated to 70° C. for 45 min. The mixture was cooled to room temperature, charged with Norit A charcoal (5 g) and filtered through celite. The filtrate was then concentrated in vacuo affording (S)-methyl 1-(1,3-benzodioxol-5-yl)-3-[4-methoxy-2-[2-(phenylmethoxy)ethoxy]phenyl]-5-propoxy-1H-indene-2-carboxylate as a yellow gum (640 mg, 98% yield).

Workup

  1. temperatureheated to 70° C. for 45 min
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-fcad490ddefc497c8d70273e11b21ef8
Source dataset
uspto-grants-2002_03
Patent number
US06355813B1

Reaction notes

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