Triethylamine → {(S)-6-[(R)-7-Fluoro-4-phenoxy-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

HRID 2408529Notes

Reaction equation

HRID 2408529 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10](=[O:33])[CH2:11][C@H:12]1[C:16]2[CH:17]=[CH:18][C:19]([O:21][C@H:22]3[C:30]4[C:25](=[C:26]([OH:32])[CH:27]=[CH:28][C:29]=4[F:31])[CH2:24][CH2:23]3)=[CH:20][C:15]=2[O:14][CH2:13]1.[C:34]1(B(O)O)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[CH3:8][O:9][C:10](=[O:33])[CH2:11][C@H:12]1[C:16]2[CH:17]=[CH:18][C:19]([O:21][C@H:22]3[C:30]4[C:25](=[C:26]([O:32][C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[CH:27]=[CH:28][C:29]=4[F:31])[CH2:24][CH2:23]3)=[CH:20][C:15]=2[O:14][CH2:13]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 86720104[(S)-6-((R)-7-Fluoro-4-hydroxyindan-1-yloxy)-2,3-dihydrobenzofuran-3-yl]-acetic acid methyl ester

Product 1

HCID 86720105{(S)-6-[(R)-7-Fluoro-4-phenoxy-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.4 mL) is added to a mixture of {(S)-6-[(R)-7-fluoro-4-hydroxy-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (0.15 g), phenylboronic acid (0.10 g), freshly activated molecular sieves 4A (1.0 g), copper(II) acetate (78 mg) and dichloromethane (8 mL) at room temperature. The flask is purged with O2 and sealed. The mixture is stirred under O2 atmosphere (1 bar) at room temperature for 16 h. The mixture is diluted with dichloromethane, filtered and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→80:20) to give the title compound. LC (method 3): tR=0.81 min; Mass spectrum (ESI+): m/z=435 [m+H]+.

Workup

  1. customThe flask is purged with O2
  2. customsealed
  3. additionThe mixture is diluted with dichloromethane
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→80:20)

Sources & evidence

ORD record
ord-9ef8a7e074154f64875a9a9305f6ccdd
Source dataset
uspto-grants-2014_08
Patent number
US08815864B2

Reaction notes

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