Methylamine → HCID 24970349, compound

HRID 1850813Notes

Reaction equation

HRID 1850813 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](N)=[N:8][C:9]2[C:14]([C:15]=1C1C=CC(C)=CC=1)=[CH:13][C:12](Br)=[CH:11][CH:10]=2)=[O:5])[CH3:2].[B-](F)(F)(F)F.[CH3:30]C([PH+](C(C)(C)C)C(C)(C)C)(C)C.[CH3:43][NH2:44].[CH2:45]1[CH2:55][CH2:54][N:53]2[C:48](=NCCC2)[CH2:47][CH2:46]1.C1C[O:59][CH2:58]C1>CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd]>[CH3:43][NH:44][C:58]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:15]2[NH:53][C:48]1[CH:47]=[CH:46][C:45]([CH3:30])=[CH:55][CH:54]=1)=[O:59]

Participants

7

Reactant 5

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 68731228HCID 68731228, compound

Product 1

HCID 24970349HCID 24970349, compound

Reagents, catalysts & solvents 1

HCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)Catalyst

Procedure

A 2-mL microwave vial was charged with 6-bromo-4-p-tolyl-aminoquinoline-3-carboxylic acid ethyl ester (0.100 mmol), Herrmann's palladacycle (trans-di(μ-acetato)-bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II), 4.7 mg, 0.0050 mmol), [(t-Bu)3PH]BF4 (5.9 mg, 0.020 mmol), Mo(CO)6 (52.8 mg, 0.20 mmol), 1.5 equiv. of methylamine (2 M in THF) and dry THF (1.0 mL). Finally, DBU (1,8-Diazabicyclo[5.4.0]undec-7-ene, 0.045 μL, 0.30 mmol) was added and the vial was immediately capped with a Teflon septum and irradiated with microwaves for 5 min at 130° C. Volatiles were removed under reduced pressure and the residue purified by column chromatography to give ethyl 6-(methylcarbamoyl)-4-[(4-methylphenyl)amino]-quinoline-3-carboxylate.

Workup

  1. customirradiated with microwaves for 5 min at 130° C
  2. customVolatiles were removed under reduced pressure
  3. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-cecd8863bdff46c59434f999747cb939
Source dataset
uspto-grants-2015_02
Patent number
US08957092B2

Reaction notes

Loading…