1,4-Dibromobutane → HCID 73294552, compound

HRID 1398050Notes

Reaction equation

HRID 1398050 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[NH2:15])[N:11]=[C:10]([CH:20]3[CH2:25][C:24]([CH3:27])([CH3:26])[O:23][C:22]([CH3:29])([CH3:28])[CH2:21]3)[CH:9]=2)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Br[CH2:40][CH2:41][CH2:42][CH2:43]Br>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]3[CH2:43][CH2:42][CH2:41][CH2:40]3)[N:11]=[C:10]([CH:20]3[CH2:25][C:24]([CH3:27])([CH3:26])[O:23][C:22]([CH3:29])([CH3:28])[CH2:21]3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 81531DiisopropylethylamineHCID 73292040HCID 73292040, compound

Product 1

HCID 73294552HCID 73294552, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 2-[5-(4-chlorophenyl)-3-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)-1H-pyrazol-1-yl]aniline (Example 62) (25 mg, 0.06 mmol, 1 eq) in toluene (2 mL) was added diisopropylethylamine (0.52 mL, 0.3 mmol, 5 eq), and 1,4-dibromobutane (0.5 mL, 4.1 mmol, 69 eq) and the solution stirred at 130° C. in a vial for 2 days. Added water, extracted with DCM, dried over MgSO4 and concentrated. Purification by column chromatography (8 g) eluting with 7 to 15% EtOAc/hex gave the title compound (10.9 mg, 38%).

Workup

  1. extractionAdded water, extracted with DCM
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customPurification by column chromatography (8 g)
  5. washeluting with 7 to 15% EtOAc/hex

Sources & evidence

ORD record
ord-ea26f61a15c94f3ca30a1b200c9b19cd
Source dataset
uspto-grants-2014_12
Patent number
US08901314B2

Reaction notes

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