3-Phenyl-propyldisulfanyl-3-propylbenzene → HCID 178420272, compound

HRID 660150Notes

Reaction equation

HRID 660150 reaction equation
[CH3:1][S:2][C:3]1[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[N:5][NH:6][CH:7]=1.[C:14]1([C:20]2(CCC)C=CC=C(SSCCC)[CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.BrC1C(C2C=NC=CC=2)=NNC=1>C(OCC)(=O)C>[C:14]1([CH2:20][CH2:21][CH2:1][S:2][C:3]2[C:4]([C:8]3[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=3)=[N:5][NH:6][CH:7]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 866262103-Phenyl-propyldisulfanyl-3-propylbenzeneHCID 178419464HCID 178419464, compound2×HCID 178503312HCID 178503312, compound

Product 1

HCID 178420272HCID 178420272, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Compound 21I was prepared following the procedure as described for the synthesis of compound 21A (see Scheme 3) using 3-phenyl-propyldisulfanyl-3-propylbenzene as the disulfide (prepared according to the methodology described in Tetrahedron Letters, 42, 2001, 6741-6743) and 3-(4-bromo-1H-pyrazol-3-yl)-pyridine (compound 20A). (conditions flash chromatography (ethyl acetate)) Yield: 22% (oil). 1H-NMR (400 MHz, CDCl3): δ 9.18 (d, J=2 Hz, 1H), 8.62 (dd, J=5 Hz, 2 Hz, 1H), 8.31 (dt, J=8 Hz, 2 Hz, 1H), 7.69 (s, 1H), 7.40-7.36 (m, 1H), 7.24 (bt, J=7 Hz, 2H), 7.17 (bt, J=7 Hz, 1H), 7.04 (bd, J=7 Hz, 2H), 2.65-2.57 (m, 4H), 1.84-1.75 (m, 2H).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-780b3b94ed4f42adb4e03b08ef1190e5
Source dataset
uspto-grants-2011_12
Patent number
US08084473B2

Reaction notes

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