Triethylamine → HCID 58201231, compound

HRID 1944422Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[C:12]([CH2:16][C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([F:26])[CH:24]=4)[N:19]([CH2:27][C:28]([OH:30])=[O:29])[C:18]=3[CH3:31])=[CH:13][S:14][CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C>[Pd].C(O)C>[C:5]1([S:8]([C:11]2[C:12]([CH2:16][C:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([F:26])[CH:24]=4)[N:19]([CH2:27][C:28]([OH:30])=[O:29])[C:18]=3[CH3:31])=[CH:13][S:14][CH:15]=2)(=[O:10])=[O:9])[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of {3-[4-(4-chlorobenzenesulfonyl)thiophen-3-ylmethyl]-5-fluoro-2-methylindol-1-yl}acetic acid (0.031 g), triethylamine (0.300 mL), palladium on charcoal (0.012 g) and ethanol (5.0 mL) was stirred under an atmosphere of hydrogen at 40° C. for 15 hours. The mixture was filtered through Celite and the filtrate concentrated under reduced pressure. The residue was purified by preparative reverse-phase HPLC, eluting with a mixture of acetonitrile and water (1:19 to 49:1 by volume) to afford the title compound as a pale yellow solid (0.024 g).

Workup

filtrationThe mixture was filtered through Celite
concentrationthe filtrate concentrated under reduced pressure
customThe residue was purified by preparative reverse-phase HPLC
washeluting with a mixture of acetonitrile and water (1:19 to 49:1 by volume)

Sources & evidence

ORD record: ord-eb7591f85177451ca718eff66cbce10e
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394836B2

Reaction notes

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