5-Bromo-2-nitrobenzotrifluoride → HCID 67171572, compound

HRID 872549Notes

Reaction equation

HRID 872549 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[O:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[N:21]1[C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][CH:23]=[N:22]1>>[N+:12]([C:5]1[CH:4]=[CH:3][C:2]([C:25]2[N:21]([CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][O:15]3)[N:22]=[CH:23][CH:24]=2)=[CH:7][C:6]=1[C:8]([F:11])([F:10])[F:9])([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 1361715-Bromo-2-nitrobenzotrifluorideHCID 115872081-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 67171572HCID 67171572, compoundYield 61.7%

Procedure

The title compound was prepared from 5-bromo-2-nitrobenzotrifluoride (5 g, 18.52 mmol) and 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (5.67 g, 20.37 mmol) using the method of Example 34(a). Reaction afforded 3.90 g of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.49-1.68 (m, 3H), 1.82 (m, 1H), 1.94 (m, 1H), 2.38 (m, 1H), 3.61 (m, 1H), 3.99 (d, 1H), 5.31 (m, 1H), 6.78 (d, 1H), 7.66 (d, 1H), 8.10 (m, 1H), 8.19 (m, 1H), 8.32 (d, 1H).

Workup

  1. customReaction

Sources & evidence

ORD record
ord-2b031a6731de4050b76796df8ebf42c2
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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