Triethylamine → HCID 22909957, compound

HRID 1379280Notes

Reaction equation

HRID 1379280 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[Br:19][CH:20]([CH2:24][CH2:25][Br:26])[C:21](Cl)=[O:22]>O1CCCC1.Cl>[Br:19][CH:20]([CH2:24][CH2:25][Br:26])[C:21]([NH:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:5]=[CH:4][N:3]=1)=[O:22]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27783152-Amino-4-(trifluoromethyl)pyridineHCID 44131432,4-Dibromobutyryl chloride

Product 1

HCID 22909957HCID 22909957, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-amino-4-trifluoromethylpyridine (5.00 g) and triethylamine (3.43 g) in dry tetrahydrofuran (50 ml) was added dropwise, over ten minutes, to a stirred solution of 2,4-dibromobutanoyl chloride (9.51 g) in dry tetrahydrofuran (50 ml), whilst maintaining the temperature below 5° C. The mixture was allowed to stir overnight at room temperature, diluted with hydrochloric acid (1M) and extracted with ethyl acetate. The extracts were washed with brine, dried over magnesium sulphate and evaporated under reduced pressure. The residue was chromatographed on silica, using hexane-ethyl acetate (5:1) as eluant, to give the title compound (10.09 g, yellow gum) sufficiently pure for use in Step 2 below. Rechromatographed material had NMR (CDCl3): δ 2.57(1H,m); 2.74(1H,m); 3.62(2H,m); 4.71(1H,dd); 7.33(1H,dd); 8.49(3H,d+s); 8.84(1H,bs). MS: M+ 388.

Workup

  1. temperaturewhilst maintaining the temperature below 5° C
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-fa0bf92c73844d1cb772564055bdc5f3
Source dataset
uspto-grants-1997_09
Patent number
US05670656

Reaction notes

Loading…