2-Methoxyethylamine → HCID 68574928, compound

HRID 1949026Notes

Reaction equation

HRID 1949026 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[C:4]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[O:22][CH3:23])[CH:3]=1.[CH3:24][O:25][CH2:26][CH2:27][NH2:28]>O1CCOCC1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[O:22][CH3:23])[CH:3]=[C:2]2[NH:28][CH2:27][CH2:26][O:25][CH3:24]

Participants

6

Reactant 2

HCID 80182-MethoxyethylamineHCID 68574873HCID 68574873, compound

Product 1

HCID 68574928HCID 68574928, compound

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

(4-Bromo-6-chloro-quinolin-2-yl)-(4-fluoro-2-methoxy-benzyl)-amine (prepared from 2-amino-6-chloro-4-hydroxyquinoline and 4-fluoro-2-methoxybenzaldehyde as described in example 30, step A and B, 328 mg, 0.828 mmol) was dissolved in 5 mL dioxane. Argon was bubbled through the solution for 2 minutes to remove oxygen. 2-Methoxyethylamine (187 mg, 2.49 mmol), sodium tert.-butylate (159 mg, 1.66 mmol), 1,1′-bis(diphenylphosphino)ferrocene (69 mg, 0.125 mmol) and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride (34 mg, 0.042 mmol) were added. The reaction mixture was stirred in a sealed tube at 100° C. for 2 h. The solvent was evaporated and the residue purified by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0->110:10:1 gradient). 6-Chloro-N2-(4-fluoro-2-methoxy-benzyl)-N4-(2-methoxy-ethyl)-quinoline-2,4-diamine was obtained as an off-white foam (285 mg, 88%), MS: m/e=390.0 (M+H+).

Workup

  1. customArgon was bubbled through the solution for 2 minutes
  2. customto remove oxygen
  3. customThe solvent was evaporated
  4. customthe residue purified by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0->110:10:1 gradient)

Sources & evidence

ORD record
ord-a75798a1a74842f89d0b81ec7109db98
Source dataset
uspto-grants-2013_03
Patent number
US08399674B2

Reaction notes

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