Triethylamine → HCID 117771406, compound

HRID 2201526Notes

Reaction equation

HRID 2201526 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.[Br:10][C:11]1[N:16]=[C:15]([C:17](O)=[O:18])[C:14]([O:20][CH3:21])=[CH:13][CH:12]=1.C(N(CC)CC)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(Cl)Cl.O>[Br:10][C:11]1[N:16]=[C:15]([C:17]([NH:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:18])[C:14]([O:20][CH3:21])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 660364-ChlorobenzylamineHCID 111923Propylphosphonic anhydrideHCID 714639656-Bromo-3-methoxypyridine-2-carboxylic acid

Product 1

HCID 117771406HCID 117771406, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-chlorophenyl)methanamine (610 mg, 4.31 mmol), 6-bromo-3-methoxypicolinic acid (1.0 g, 4.31 mmol) and triethylamine (1.31 g, 12.9 mmol) in DCM (10 mL) was added dropwise T3P (2.74 g, 8.61 mmol) at 0° C. Five minutes later, TLC indicated the reaction was complete, and the mixture was suspended in water and extracted with DCM. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo to give the crude 6-bromo-N-(4-chlorobenzyl)-3-methoxypicolinamide (1.3 g, yield: 87%) without further purification. 1H-NMR (DMSO-d6, 400 MHz) δ 8.98 (t, J=6.0 Hz, 1H), 7.69 (d, J=8.8 Hz, 1H), 7.58 (d, J=8.8 Hz, 1H), 7.39˜7.43 (m, 2H), 7.33 (d, J=8.4 Hz, 2H), 4.22 (d, J=6.4 Hz, 2H), 3.84 (s, 3H). MS (M+H)+: 355/357.

Workup

  1. customFive minutes
  2. extractionextracted with DCM
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05e6393fd5374acc85faaf7786881df4
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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