(Pent-4-yn-1-yl)cyclohexane → 3-[1-phenylsulfonyl-4-(5-cyclohexyl-pent-1-ynyl)-1H-pyrazol-3-yl]-pyridine

HRID 660164Notes

Reaction equation

HRID 660164 reaction equation
[C:1]([C:7]1[C:8]([C:12]2[CH2:13][N:14](C)[CH2:15][CH2:16][CH:17]=2)=[N:9][NH:10][CH:11]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:19]([CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[CH2:20][CH2:21][C:22]#[CH:23].[C:30]1([S:36]([N:39]2[CH:43]=[C:42](I)[C:41]([C:45]3[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=3)=[N:40]2)(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(OCC)C>[CH:6]1([CH2:5][CH2:4][CH2:3][C:2]#[C:1][C:7]2[C:8]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)=[N:9][NH:10][CH:11]=2)[CH2:25][CH2:24][CH2:19][CH2:20][CH2:21]1.[C:30]1([S:36]([N:39]2[CH:43]=[C:42]([C:23]#[C:22][CH2:21][CH2:20][CH2:19][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[C:41]([C:45]3[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=3)=[N:40]2)(=[O:37])=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 15172912(Pent-4-yn-1-yl)cyclohexaneHCID 575480663-(1-phenylsulfonyl-4-iodo-1H-pyrazol-3-yl)-pyridineHCID 1784424703-(4-Hex-1-ynyl-1H-pyrazol-3-yl)-1,2,5,6-tetrahydro-1-methylpyridine

Product 2

HCID 672842613-[1-phenylsulfonyl-4-(5-cyclohexyl-pent-1-ynyl)-1H-pyrazol-3-yl]-pyridineYield 90%HCID 178437213HCID 178437213, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Compound 44E was prepared following the procedure as described for the synthesis of compound 44A (see Scheme 9) using pent-4-ynyl-cyclohexane and 3-(1-phenylsulfonyl-4-iodo-1H-pyrazol-3-yl)-pyridine (36B). (flash chromatography with diethyl ether/PE 1/1) to afford 3-[1-phenylsulfonyl-4-(5-cyclohexyl-pent-1-ynyl)-1H-pyrazol-3-yl]-pyridine (43E) as an oil (90%). 1H-NMR (400 MHz, CDCl3) δ 9.25 (d, J=2 Hz, 1H), 8.6 (dd, J=5 Hz, 2 Hz, 1H), 8.33 (dt, J=8 Hz, 2 Hz, 1H), 8.21 (s, 1H), 8.08-8.04 (m, 2H), 7.68 (bt, J=8 Hz, 1H), 7.57 (bt, J=8 Hz, 2H), 7.35-7.31 (m, 1H), 2.38 (t, J=7 Hz, 2H), 1.72-1.55 (m, 6H), 1.31-1.10 (m, 7H), 0.95-0.8 (m, 2H).

Sources & evidence

ORD record
ord-60c1e8f2a81c4b7d8840a02ed4f77e56
Source dataset
uspto-grants-2011_12
Patent number
US08084473B2

Reaction notes

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