2-Bromo-3-methoxypyridine → HCID 23045060, compound

HRID 2108036Notes

Reaction equation

HRID 2108036 reaction equation
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:10][C:11]1[C:16]([Cl:17])=[CH:15][C:14]([CH:18]([CH2:20][N:21]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][CH2:29][C:30]#[CH:31])[OH:19])=[CH:13][C:12]=1[Cl:39]>C(NCC)C.C1COCC1.[Cu]I>[NH2:10][C:11]1[C:12]([Cl:39])=[CH:13][C:14]([CH:18]([CH2:20][N:21]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][CH2:29][C:30]#[C:31][C:2]2[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[OH:19])=[CH:15][C:16]=1[Cl:17]

Participants

6

Reactant 2

HCID 903642-Bromo-3-methoxypyridineHCID 200628464-Amino-3,5-dichloro-alpha-[[(phenylmethyl)[6-[(2-propynyl)oxy]hexyl]amino]methyl]benzenemethanol

Product 1

HCID 23045060HCID 23045060, compoundYield 77.7%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8021DiethylamineSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromo-3-methoxypyridine (2 g), 4-amino-3,5-dichloro-α-[[(phenylmethyl)[6-[(2-propynyl)oxy]hexyl]amino]methyl]benzenemethanol (5.74 g), BTPC (150 mg), copper (I) iodide (15 mg) in diethylamine (20 ml) and THF (10 ml) was stirred under nitrogen overnight. The solution was concentrated in vacuo to give a brown oil which was purified by FCC eluting with System C (95:5:1) to give the title compound as a brown oil (4.6 g), t.l.c. (System A 80:20:1) Rf 0.6.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customto give a brown oil which
  3. customwas purified by FCC
  4. washeluting with System C (95:5:1)

Sources & evidence

ORD record
ord-77ec110885904cf684a73fe2a1086a4b
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

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