Sodium Carbonate → N-(1-(3-(4-Cyanophenyl)-7-fluoro-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)ethyl)-N-(2-(ethylsulfonyl)ethyl)-2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamide

HRID 1715039Notes

Reaction equation

HRID 1715039 reaction equation
Br[C:2]1[C:7](=[O:8])[N:6]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:5]2=[N:4][C:3]=1[CH:14]([N:16]([CH2:31][CH2:32][S:33]([CH2:36][CH3:37])(=[O:35])=[O:34])[C:17](=[O:30])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:20]=1)[CH3:15].[C:38]([C:40]1[CH:45]=[CH:44][C:43](B(O)O)=[CH:42][CH:41]=1)#[N:39].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1COCC1>[C:38]([C:40]1[CH:45]=[CH:44][C:43]([C:2]2[C:7](=[O:8])[N:6]3[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:5]3=[N:4][C:3]=2[CH:14]([N:16]([CH2:31][CH2:32][S:33]([CH2:36][CH3:37])(=[O:35])=[O:34])[C:17](=[O:30])[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:20]=2)[CH3:15])=[CH:42][CH:41]=1)#[N:39]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 58796903N-(1-(3-Bromo-7-fluoro-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)ethyl)-N-(2-(ethylsulfonyl)ethyl)-2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamide

Product 1

HCID 16040357N-(1-(3-(4-Cyanophenyl)-7-fluoro-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)ethyl)-N-(2-(ethylsulfonyl)ethyl)-2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamideYield 54.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

E5 (66.8 mg, 0.11 mmol), 4-cyanophenyl boronic acid (20 mg, 0.13 mmol), and Pd(dppf)2Cl2 (9 mg, 0.01 mmol) was added into a 10 mL CEM microwave tube, followed by THF (1.1 mL) and sodium carbonate (0.55 mL, 2M). The mixture was reacted by microwave at 150° C. for 10 min and then partitioned between water and ethyl acetate. Column chromatography with gradient dichloromethane:ethyl acetate (4:1 to 3:1 to 2:1) afforded 38 mg 7.01 as a yellow foamy solid in a racemic mixture. Additional amounts of 7.01 were prepared and combined.

Workup

  1. customThe mixture was reacted by microwave at 150° C. for 10 min
  2. custompartitioned between water and ethyl acetate

Sources & evidence

ORD record
ord-20e5da98d45d429ba00c1f45c9a72cd3
Source dataset
uspto-grants-2010_09
Patent number
US07799795B2

Reaction notes

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