Sodium Carbonate → HCID 50906138, compound

HRID 1431297Notes

Reaction equation

HRID 1431297 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]([CH3:18])=[C:16]([NH:19][C:20]2[CH:25]=[C:24](B3OC(C)(C)C(C)(C)O3)[CH:23]=[CH:22][C:21]=2[N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.Br[C:42]1[CH:47]=[CH:46][N:45]=[C:44]([NH2:48])[CH:43]=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>[NH2:48][C:44]1[CH:43]=[C:42]([C:24]2[CH:23]=[CH:22][C:21]([N:35]3[CH2:36][CH2:37][O:38][CH2:39][CH2:40]3)=[C:20]([NH:19][C:16]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[N:9]=[C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])[C:17]=3[CH3:18])[CH:25]=2)[CH:47]=[CH:46][N:45]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 6932822-Amino-4-bromopyridineHCID 59631147HCID 59631147, compound

Product 1

HCID 50906138HCID 50906138, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(2-fluorophenyl)-3-methyl-N-(2-morpholino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinolin-4-amine (44.0 mg, 0.082 mmol), 4-bromopyridin-2-amine (14.1 mg, 0.082 mmol), dichlorobis(triphenylphosphine)palladium(II) (5.73 mg, 8.16 μmol) and sodium carbonate (14.68 mg, 0.245 mmol) in 1,4-dioxane (2.00 mL) and water (0.500 mL) in a microwave vessel was purged with nitrogen then heated in a microwave at 120° C. for 60 min, after which time LC-MS indicated no starting material remained and desired product was present. The reaction was partitioned between 30 mL EtOAc and 20 mL water. The organic separation was stirred over anhydrous magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a yellow film. The product was isolated by preparative scale reversed-phase HPLC, affording a colorless solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.11 (1H, d, J=8.2 Hz), 7.92 (1H, d, J=5.5 Hz), 7.84 (1H, d, J=8.6 Hz), 7.60-7.69 (1H, m), 7.56 (1H, td, J=7.4, 2.0 Hz), 7.34-7.51 (2H, m), 7.26 (1H, t, J=7.4 Hz), 6.99-7.21 (5H, m), 6.63 (2H, dd, J=7.4, 2.3 Hz), 6.43 (1H, br. s.), 4.44 (2H, d, J=1.2 Hz), 3.88 (4H, t, J=4.7 Hz), 2.94-3.23 (4H, m), 2.15 (3H, d, J=2.3 Hz). Mass Spectrum (ESI) m/e=506.2 (M+1).

Workup

  1. customwas purged with nitrogen
  2. customThe reaction was partitioned between 30 mL EtOAc and 20 mL water
  3. customThe organic separation
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customto afford a yellow film
  7. customThe product was isolated by preparative scale reversed-phase HPLC
  8. customaffording a colorless solid

Sources & evidence

ORD record
ord-a16f255f2c794a55a151a691d8958945
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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