1-Heptyne → 3-(1-phenylsulfonyl-4-hept-1-ynyl-1H-pyrazol-3-yl)-pyridine

HRID 1027530Notes

Reaction equation

HRID 1027530 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][CH3:25].[C:26]1([S:32]([N:35]2[CH:39]=[C:38](Br)[C:37]([C:41]3[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=3)=[N:36]2)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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][CH3:19].[C:26]1([S:32]([N:35]2[CH:39]=[C:38]([C:19]#[C:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:37]([C:41]3[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=3)=[N:36]2)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 123501-HeptyneHCID 575480773-(1-Phenylsulfonyl-4-bromo-1H-pyrazol-3-yl)-pyridineHCID 1784424703-(4-Hex-1-ynyl-1H-pyrazol-3-yl)-1,2,5,6-tetrahydro-1-methylpyridine

Product 2

HCID 672844283-(1-phenylsulfonyl-4-hept-1-ynyl-1H-pyrazol-3-yl)-pyridineYield 90%HCID 178442542HCID 178442542, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Compound 44B was prepared following the procedure as described for the synthesis of compound 44A (see Scheme 9) using hept-1-yne and 3-(1-phenylsulfonyl-4-bromo-1H-pyrazol-3-yl)-pyridine (36A). (flash chromatography with diethyl ether) to afford 3-(1-phenylsulfonyl-4-hept-1-ynyl-1H-pyrazol-3-yl)-pyridine (43B) as an oil (90%). 1H-NMR (400 MHz, CDCl3): δ 925 (bs, 1H), 8.6 (bs, 1H), 8.34 (bd, J=8 Hz, 1H), 8.21 (s, 1H), 8.06 (bd, J=8 Hz, 2H), 7.67 (bt, J=7 Hz, 1H), 7.57 (bt, J=7 Hz, 2H), 7.36-7.30 (m, 1H), 2.42 (t, J=7 Hz, 2H), 1.63-1.55 (m, 2H), 1.44-1.28 (m, 4H), 0.89 (t, J=7 Hz, 3H). Compound 43B was converted to the title compound 44B, using the methodology described for the conversion of 43A to 44A (see Scheme 9). Yield: 98% (oil). 1H-NMR (400 MHz, CDCl3): δ 9.25 (d, J=2 Hz, 1H), 8.59 (dd, J=5 Hz, 2 Hz, 1H), 8.37 (dt, J=8 Hz, 2 Hz, 1H), 7.72 (s, 1H), 7.38-7.33 (m, 1H), 2.42 ((t, J=7 Hz, 2H), 1.65-1.57 (m, 2H), 1.46-1.30 (m, 4H), 0.90 (t, J=7 Hz, 3H).

Sources & evidence

ORD record
ord-d7ccb12464c04be790579e4a1af7cd00
Source dataset
uspto-grants-2014_05
Patent number
US08735388B2

Reaction notes

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