Potassium Carbonate → 1-Benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid [6-(4-dimethylamino-phenyl)-pyridin-yl]-amide

HRID 1505125Notes

Reaction equation

HRID 1505125 reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2([C:14]3[CH:22]=[CH:21][C:17]4[O:18][CH2:19][O:20][C:16]=4[CH:15]=3)[CH2:13][CH2:12]2)=[O:10])[CH:5]=[CH:4][CH:3]=1.[CH3:23][N:24]([CH3:34])[C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.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]>[CH3:23][N:24]([CH3:34])[C:25]1[CH:30]=[CH:29][C:28]([C:2]2[N:7]=[C:6]([NH:8][C:9]([C:11]3([C:14]4[CH:22]=[CH:21][C:17]5[O:18][CH2:19][O:20][C:16]=5[CH:15]=4)[CH2:13][CH2:12]3)=[O:10])[CH:5]=[CH:4][CH:3]=2)=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343444-(Dimethylamino)phenylboronic acidHCID 591658951-(Benzo[d][1,3]dioxol-6-yl)-N-(6-bromopyridin-2-yl)cyclopropanecarboxamide

Product 1

HCID 166794271-Benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid [6-(4-dimethylamino-phenyl)-pyridin-yl]-amide

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1-Benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid (6-bromo-pyridin-2-yl)-amide (36 mg, 0.10 mmol) was dissolved in 1 mL of N,N-dimethylformamide in a reaction tube. 4-(Dimethylamino)phenylboronic acid (21 mg, 0.13 mmol), 0.1 mL of an aqueous 2M potassium carbonate solution, and (Pd(dppf)Cl2 (6.6 mg, 0.0090 mmol) were added and the reaction mixture was heated at 80° C. for three hours. The resulting material was cooled to room temperature, filtered, and purified by reverse-phase preparative liquid chromatography to yield the pure product as a trifluoroacetic acid salt. ESI-MS m/z calc. 401.2, found 402.5 (M+1)+. Retention time 2.96 minutes. 1H NMR (400 MHz, CD3CN) δ 1.23-1.27 (m, 2H), 1.62-1.66 (m, 2H), 3.04 (s, 6H), 6.06 (s, 2H), 6.88-6.90 (m, 2H), 6.93-6.96 (m, 1H), 7.05-7.07 (m, 2H), 7.53-7.56 (m, 1H), 7.77-7.81 (m, 3H), 7.84-7.89 (m, 1H), 8.34 (s, 1H).

Workup

  1. temperatureThe resulting material was cooled to room temperature
  2. filtrationfiltered
  3. custompurified by reverse-phase preparative liquid chromatography

Sources & evidence

ORD record
ord-52f5dcf68c9945da9d009d9db9fd0bf0
Source dataset
uspto-grants-2015_12
Patent number
US09216969B2

Reaction notes

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