1,4-Dibromobutane → HCID 68655795, compound

HRID 2369057Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])(=O)=[O:25])[CH:19]=3)=[CH:16][CH:17]=2)=[CH:11][C:10]([C:28]([NH2:31])([CH3:30])[CH3:29])=[N:9]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:39][CH2:40][CH2:41][CH2:42]Br>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([S:24]([CH3:27])=[O:25])[CH:19]=3)=[CH:16][CH:17]=2)=[CH:11][C:10]([C:28]([CH3:29])([N:31]2[CH2:42][CH2:41][CH2:40][CH2:39]2)[CH3:30])=[N:9]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of the 2-[1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-2-thienyl}-1H-pyrazol-3-yl]propan-2-amine (142 mg, 0.3 mmol), K2CO3 (83 mg, 0.6 mmol), 1,4-dibromobutane (0.1 mL, 0.7 mmol) and anhydrous EtOH was stirred at 100° C. in a sealed vial for 18 h. The solvent was removed in vacuo, and the residue was purified by flash chromatography (0-40% 20% MeOH/DCM) to give the title compound as a pale-yellow solid. 1HNMR (CDCl3): Et 8.03 (m, 1H), 7.86-7.83 (m, 1H), 7.74-7.71 (m, 1H), 7.61-7.47 (m, 5H), 7.23 (d, 1H), 6.93 (s, 1H), 6.83 (d, 1H), 3.68 (m, 2H), 3.08 (s, 3H), 2.17 (m, 2H), 2.04 (s, 6H), 1.83 (m, 2H). MS(ES): 526 [M+H]+.

Workup

customThe solvent was removed in vacuo
customthe residue was purified by flash chromatography (0-40% 20% MeOH/DCM)

Sources & evidence

ORD record: ord-3c99dd68671c4e18bc02f66d4f8c1890
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703805B2

Reaction notes

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