Sodium Carbonate → HCID 50938827, compound

HRID 1618548Notes

Reaction equation

HRID 1618548 reaction equation
[CH3:1][C:2]1([CH3:42])[C:6]2=[N:7][CH:8]=[C:9](B3OC(C)(C)C(C)(C)O3)[CH:10]=[C:5]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][C:32]=3[S:37]([CH3:40])(=[O:39])=[O:38])[C:21]=2[CH3:41])[CH2:3]1.[NH2:43][C:44]1[N:49]=[C:48](Cl)[CH:47]=[CH:46][N:45]=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:6](=[N:7][CH:8]=[C:9]([C:46]5[CH:47]=[CH:48][N:49]=[C:44]([NH2:43])[N:45]=5)[CH:10]=4)[C:2]([CH3:1])([CH3:42])[CH2:3]3)=[C:21]([CH3:41])[C:22]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[S:37]([CH3:40])(=[O:38])=[O:39])=[N:23]2)=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2233322-Amino-4-chloropyrimidineHCID 67284521HCID 67284521, compound

Product 1

HCID 50938827HCID 50938827, compound

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)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)quinoline (131 mg, 0.22 mmol) (described herein), 2-amino-4-chloropyrimidine (28.9 mg, 0.22 mmol), bis(triphenylphosphine)palladium(ii) chloride (15.7 mg, 0.022 mmol), and sodium carbonate (70.9 mg, 0.67 mmol) in 1,4-dioxane (4.8 mL) and water (1.2 mL). The reaction mixture was heated in a microwave at 120° C. for 60 min. Purification afforded 4-(1-(7-fluoro-3-methyl-2-(2-(methylsulfonyl)phenyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-6-yl)-2-pyrimidinamine as a yellow solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.55 (1H, m), 8.11-8.35 (2H, m), 8.04 (1H, m), 7.64-7.91 (3H, m), 7.44-7.57 (1H, m), 7.20-7.44 (2H, m), 6.70-7.05 (1H, m), 4.9-5.35 (2H, m), 3.35-3.96 (2H, m), 2.97-3.22 (3H, m), 1.87-2.05 (3H, m), 1.44-1.73 (6H, m). Mass Spectrum (ESI) m/e=555 (M+1).

Workup

  1. customPrepared
  2. customPurification

Sources & evidence

ORD record
ord-13df63fd61fe40f98cc6d3860346074c
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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