Diethyl Ether → 3-[1-phenylsulfonyl-4-(5-phenyl-pent-1-ynyl)-1H-pyrazol-3-yl]-pyridine

HRID 2043046Notes

Reaction equation

HRID 2043046 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]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH: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>CCOCC.C(OCC)(=O)C>[C:1]([C:7]1[C:8]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[N:9][NH:10][CH:11]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:20][CH2:19][CH3:24].[C:30]1([S:36]([N:39]2[CH:43]=[C:42]([C:23]#[C:22][CH2:21][CH2:20][CH2:19][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=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

7

Reactant 4

HCID 3283Diethyl EtherHCID 745735-Phenyl-1-pentyneHCID 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 672840863-[1-phenylsulfonyl-4-(5-phenyl-pent-1-ynyl)-1H-pyrazol-3-yl]-pyridineYield 80%HCID 1784427403-(4-Non-1-ynyl-1H-pyrazol-3-yl)-pyridine

Reagents, catalysts & solvents 1

HCID 21584169Diethylether ethylacetateSolvent

Procedure

Compound 44C was prepared following the procedure as described for the synthesis of compound 44A (see Scheme 9) using pent-4-ynyl-benzene 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-phenyl-pent-1-ynyl)-1H-pyrazol-3-yl]-pyridine (43D) as an oil (80%). 1H-NMR (400 MHz, CDCl3): δ 9.3 (d, J=2 Hz, 1H), 8.6 (dd, J=5 Hz, 2 Hz, 1H), 8.33 (dt, J=8 Hz, 2 Hz, 1H), 8.22 (s, 1H), 8.09-8.05 (m, 2H), 7.68 (bt, J=8 Hz, 1H), 7.57 (bt, J=8 Hz, 2H), 7.35-7.25 (m, 3H), 7.21-7.15 (m, 3H), 2.74 ((t, J=7 Hz, 2H), 2.42 ((t, J=7 Hz, 2H), 1.96-1.87 (m, 2H). (TLC diethyl ether Rf 0.56).

Sources & evidence

ORD record
ord-36d3ee0fa8b34b63b2025ade0ba1abb7
Source dataset
uspto-grants-2013_11
Patent number
US08586606B2

Reaction notes

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