Toluene → HCID 21886118, compound

HRID 723240Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:12]=[C:13]([C:18]#[N:19])[S:14][C:15]=2[S:16][CH3:17])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>CC([O-])=O.CC([O-])=O.[Pd+2].CO.C(Cl)(Cl)Cl>[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:2]2[CH:3]=[C:4]([S:8]([C:11]3[CH:12]=[C:13]([C:18]#[N:19])[S:14][C:15]=3[S:16][CH3:17])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=2)[CH2:23][CH2:22]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a flask containing 0.15 g (0.4 mmol) of 4-(3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carbonitrile (Example 286: step f), 44.1 μL (0.4 mmol) of N-methylpiperazine, 4.5 mg (0.02 mmol) of Pd(OAc)2, 24.8 mg (0.04 mmol) of BINAP, and 195 mg (0.6 mmol) of CsCO3 was added 2.5 mL of toluene. The flask was purged with Ar, and heated to 100° C. for 16 h. The reaction was then concentrated in vacuo and purified by preparative TLC (50%-EtOAc-Hexane), isolating the low Rf material, which was subjected to preparative TLC again (10% MeOH-CHCl3) to give 15.5 mg (10% yield) of 4-[3-(4-methyl-piperazin-1-yl)-benzenesulfonyl]-5-methylsulfanyl-thiophene-2-carbonitrile in greater than 98% purity.

Workup

customThe flask was purged with Ar
concentrationThe reaction was then concentrated in vacuo
custompurified by preparative TLC (50%-EtOAc-Hexane)
customisolating the low Rf material, which

Sources & evidence

ORD record: ord-254a295acd314604893387c0d19adacb
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138530B2

Reaction notes

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