Sodium Carbonate → 4-(1-(7-Fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-6-methyl-2-pyrimidinamine

HRID 1618539Notes

Reaction equation

HRID 1618539 reaction equation
[CH3:1][C:2]1([CH3:38])[C:10]2[C:5](=[CH:6][C:7](B3OC(C)(C)C(C)(C)O3)=[CH:8][CH:9]=2)[N:4]([C:20]2[C:29]3[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=3)[N:23]=[C:22]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)[C:21]=2[CH3:37])[CH2:3]1.Cl[C:40]1[CH:45]=[C:44]([CH3:46])[N:43]=[C:42]([NH2:47])[N:41]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:30][C:26]1[CH:25]=[C:24]2[C:29]([C:20]([N:4]3[C:5]4[C:10](=[CH:9][CH:8]=[C:7]([C:40]5[CH:45]=[C:44]([CH3:46])[N:43]=[C:42]([NH2:47])[N:41]=5)[CH:6]=4)[C:2]([CH3:38])([CH3:1])[CH2:3]3)=[C:21]([CH3:37])[C:22]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)=[N:23]2)=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 218102-Amino-4-chloro-6-methylpyrimidineHCID 672857464-(3,3-Dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-1-yl)-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline

Product 1

HCID 509388294-(1-(7-Fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-6-methyl-2-pyrimidinamine

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

Prepared according to procedure P using 4-(3,3-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-1-yl)-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (70 mg, 0.14 mmol) (described herein), 4-chloro-6-methylpyrimidin-2-amine (21.7 mg, 0.15 mmol), bis(triphenylphosphine)palladium(ii) chloride (9.6 mg, 0.014 mmol), and sodium carbonate (43.7 mg, 0.41 mmol) in 1,4-dioxane (3.1 mL) and water (0.79 mL), and heating in a microwave at 120° C. for 60 min. After purification 4-(1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-6-methyl-2-pyrimidinamine was obtained as a yellow solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.75 (1H, d, J=4.3 Hz), 7.76-7.96 (4H, m), 7.34-7.46 (2H, m), 7.28 (1H, br. s.), 7.21-7.26 (1H, m), 6.66-6.76 (1H, m), 6.58 (1H, d, J=1.2 Hz), 5.19 (2H, br. s.), 3.74-3.90 (2H, m), 2.35-2.41 (3H, m), 2.28-2.35 (3H, m), 1.55-1.61 (3H, m), 1.49-1.55 (3H, m). Mass Spectrum (ESI) m/e=491 (M+1).

Workup

  1. customPrepared
  2. customAfter purification 4-(1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-6-methyl-2-pyrimidinamine
  3. customwas obtained as a yellow solid

Sources & evidence

ORD record
ord-c0220da193274c81874f7a9d43520851
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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