Triethylamine → HCID 58138927, compound

HRID 2061573Notes

Reaction equation

HRID 2061573 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][NH2:13])=[CH:7][C:6]=2[Br:14].[F:17][C:18]([F:29])([F:28])[C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][N:20]=1.CCN(CC)CC>C(Cl)Cl>[F:16][C:2]([F:1])([F:15])[C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][NH:13][C:23]([C:22]1[CH:21]=[N:20][C:19]([C:18]([F:29])([F:17])[F:28])=[CH:27][CH:26]=1)=[O:24])=[CH:7][C:6]=2[Br:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27775576-(Trifluoromethyl)nicotinoyl chlorideHCID 58138929HCID 58138929, compound2×

Product 1

HCID 58138927HCID 58138927, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(2-Trifluoromethyl-7-bromo-1H-indol-5-yl)methyl]amine (Intermediate 9, 230 mg, 0.785 mmol) was dissolved in DCM (10 mL) and 6-(trifluoromethyl)nicotinoyl chloride (ABCR; 181 mg, 0.863 mmol) was added. Et3N (0.219 mL, 1.570 mmol) was added and the reaction mixture was then left to stir at room temperature for 30 min. The reaction mixture was quenched with water then the organic layer was collected, dried (MgSO4), filtered and evaporated to dryness. The resulting residues were purified by MDAP to give the title compound, (200 mg);

Workup

  1. waitthe reaction mixture was then left
  2. customThe reaction mixture was quenched with water
  3. customthe organic layer was collected
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe resulting residues were purified by MDAP

Sources & evidence

ORD record
ord-03c49797362e434ebd83521888fedd21
Source dataset
uspto-grants-2012_10
Patent number
US08283365B2

Reaction notes

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