Triethylamine → HCID 57962754, compound

HRID 541566Notes

Reaction equation

HRID 541566 reaction equation
Br[C:2]1[C:3]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:4][C:5]([CH3:16])=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:7]=1.C(N(CC)CC)C.[C:30]([C:32]1[CH:33]=[C:34]([CH:36]=[CH:37][CH:38]=1)[NH2:35])#[CH:31]>O1CCCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:35][C:34]1[CH:33]=[C:32]([C:30]#[C:31][C:2]2[C:3]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:4][C:5]([CH3:16])=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:7]=2)[CH:38]=[CH:37][CH:36]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 104682Benzenamine, 3-ethynyl-HCID 57962477HCID 57962477, compound

Product 1

HCID 57962754HCID 57962754, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl (5-bromo-2-methyl-4-morpholin-4-ylphenyl)carbamate (110 mg, 0.3 mmol), copper(I) iodide (4 mg, 0.02 mmol) and bis(triphenylphosphine)palladium(II) chloride (10 mg, 0.01 mmol) were stirred in tetrahydrofuran (0.5 mL) and triethylamine (50 μL, 0.4 mmol) was added. 3-Ethynylaniline (100 μL, 1.0 mmol) was added and the mixture was heated to 80° C. for 1 hour. The mixture was filtered through celite and purified by preparative LCMS (pH 2). The product fractions were neutralized with saturated sodium bicarbonate solution, evaporated to remove acetonitrile and extracted with ethyl acetate. The extracts were evaporated to give the desired compound (25 mg, 31%). LCMS for C24H30N3O3 (M+H)+: m/z=408.1.

Workup

  1. filtrationThe mixture was filtered through celite
  2. custompurified by preparative LCMS (pH 2)
  3. customevaporated
  4. customto remove acetonitrile
  5. extractionextracted with ethyl acetate
  6. customThe extracts were evaporated

Sources & evidence

ORD record
ord-63123a78896c4b2eb2f4dfbd757fc822
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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