Piperidine → HCID 21886727, compound

HRID 723232Notes

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.[NH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]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.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:17][S:16][C:15]1[S:14][C:13]([C:18]#[N:19])=[CH:12][C:11]=1[S:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:3]=1)(=[O:10])=[O:9]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-(3-Bromo-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carbonitrile (Example 286: step f, 200 mg, 0.534 mmol), piperidine (56 mg, 0.64 mmol), Pd(OAc)2 (24 mg, 0.11 mmol), BINAP (100 mg, 0.16 mmol) and Cs2CO3 in 2 mL of toluene under Ar was stirred at 150° C. for 16 h, then cooled to RT. The mixture was purified directly by PTLC (30% EtOAc/hexane) to give 20 mg of product as a light yellow oil: 1H-NMR (CDCl3; 400 MHz) δ 7.68 (m, 1H), 7.67 (s, 1H), 7.54–7.52 (m, 1H), 7.39–7.32 (m, 2H), 3.16–3.12 (m, 4H), 2.45 (s, 3H), 1.64–1.59 (m, 4H), 1.55–1.50 (m, 2H). Mass spectrum (ESI, m/z): Calcd. for C17H18N2O2S3, 379.1 (M+H), found 379.3.

Workup

temperaturecooled to RT
customThe mixture was purified directly by PTLC (30% EtOAc/hexane)

Sources & evidence

ORD record: ord-31c2813f7b2843d9914a5637e24947c4
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138530B2

Reaction notes

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