Sodium Carbonate → 5-chloro-4-(1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-2-pyrimidinamine

HRID 1618540Notes

Reaction equation

HRID 1618540 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[C:45]([Cl:46])=[CH:44][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>[Cl:46][C:45]1[C:40]([C:7]2[CH:6]=[C:5]3[C:10]([C:2]([CH3:38])([CH3:1])[CH2:3][N:4]3[C:20]3[C:29]4[C:24](=[CH:25][C:26]([F:30])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=4)[C:21]=3[CH3:37])=[CH:9][CH:8]=2)=[N:41][C:42]([NH2:47])=[N:43][CH:44]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 211860654,5-Dichloropyrimidin-2-amineHCID 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 509388285-chloro-4-(1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-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 (68.7 mg, 0.14 mmol) (described herein), 4,5-dichloropyrimidin-2-amine (22.1 mg, 0.14 mmol), bis(triphenylphosphine)palladium(ii) chloride (9.5 mg, 0.013 mmol), and sodium carbonate (42.9 mg, 0.41 mmol) in 1,4-dioxane (2.9 mL) and water (0.73 mL), and heating in a microwave at 120° C. for 60 min. After purification 5-chloro-4-(1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-2-pyrimidinamine was obtained as a yellow solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.74 (1H, dd, J=3.9, 1.2 Hz), 8.19 (1H, s), 7.76-7.99 (4H, m), 7.35-7.42 (1H, m), 7.28-7.30 (1H, m), 7.23-7.27 (1H, m), 7.16 (1H, dd, J=7.4, 1.2 Hz), 6.36 (1H, s), 4.94-5.21 (2H, br. s.), 3.76-3.88 (2H, m), 2.37 (3H, s), 1.58 (3H, s), 1.52 (3H, s). Mass Spectrum (ESI) m/e=511 (M+1).

Workup

  1. customPrepared
  2. customAfter purification 5-chloro-4-(1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-2-pyrimidinamine
  3. customwas obtained as a yellow solid

Sources & evidence

ORD record
ord-c3c471530a8c4fcfa6295e19d2b1de71
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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