1-Nonyne → 3-(1-phenylsulfonyl-4-non-1-ynyl-1H-pyrazol-3-yl)-pyridine

HRID 1027532Notes

Reaction equation

HRID 1027532 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].[CH:19]#[C:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[C:28]1([S:34]([N:37]2[CH:41]=[C:40](I)[C:39]([C:43]3[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=3)=[N:38]2)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(OCC)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][CH2:19][CH2:20][CH3:21].[C:28]1([S:34]([N:37]2[CH:41]=[C:40]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:39]([C:43]3[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=3)=[N:38]2)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 189371-NonyneHCID 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 672839633-(1-phenylsulfonyl-4-non-1-ynyl-1H-pyrazol-3-yl)-pyridineYield 80%HCID 1784427403-(4-Non-1-ynyl-1H-pyrazol-3-yl)-pyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Compound 44C was prepared following the procedure as described for the synthesis of compound 44A (see Scheme 9) using non-1-yne 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-non-1-ynyl-1H-pyrazol-3-yl)-pyridine (43C) as an oil (80%). (TLC diethyl ether Rf 0.44).

Sources & evidence

ORD record
ord-5b2d6d9ba38b4dc3a65c3d29f8b57d73
Source dataset
uspto-grants-2014_05
Patent number
US08735388B2

Reaction notes

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