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

HRID 2408535Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:26])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([OH:25])[CH:20]=[CH:21][C:22]=4[F:24])[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1.F[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C([O-])([O-])=O.[Cs+].[Cs+].CN(C)C=O>CN1CCCC1=O>[CH3:1][O:2][C:3](=[O:26])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19]([O:25][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=5)[CH:20]=[CH:21][C:22]=4[F:24])[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1

Participants

Conditions

Temperature: 130 °C

Procedure

A microwave vial is charged with a stir bar, {(S)-6-[(R)-7-fluoro-4-hydroxy-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (0.10 g), 2-fluoro-pyridine (27 mg), Cs2CO3 (91 mg) and N,N-dimethylformamide (2 mL; alternatively N-methyl-pyrrolidinone is used). The mixture is stirred at 130° C. for 30 min by irradiation in a microwave oven. After cooling to room temperature, the mixture is concentrated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→80:20) to give the title compound. LC (method 2): tR=1.15 min; Mass spectrum (ESI+): m/z=436 [M+H]+.

Workup

additionA microwave vial is charged with a stir bar
temperatureAfter cooling to room temperature
concentrationthe mixture is concentrated
customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→80:20)

Sources & evidence

ORD record: ord-952f1dcdecee44748a132899a701a423
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815864B2

Reaction notes

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