Potassium Carbonate → HCID 178423693, compound

HRID 2197534Notes

Reaction equation

HRID 2197534 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]4[NH:35][C:29]5=[N:30][C:31](Cl)=[CH:32][CH:33]=[C:28]5[N:27]=4)=[CH:21][CH:20]=3)[C:9]([C:11]([NH:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.B(O)(O)[C:37]1[CH:38]=[CH:39][C:40]([CH3:43])=[CH:41][CH:42]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:1][C:2]1[C:7]2=[C:8]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26]4[NH:35][C:29]5=[N:30][C:31]([C:37]6[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=6)=[CH:32][CH:33]=[C:28]5[N:27]=4)=[CH:21][CH:20]=3)[C:9]([C:11]([NH:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 178508830HCID 178508830, compound

Product 1

HCID 178423693HCID 178423693, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 4-amino-5-{4-[(5-chloro-3H-imidazo[4,5-b]pyridin-2-yl)amino]phenyl}-N-(2,2,2-trifluoroethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide (50 mg, 0.1 mmol), p-tolylboronic acid (27 mg, 0.2 mmol), potassium carbonate (82 mg, 0.6 mmol), in DMF was added 1,1′-bis(diphenylphosphino)ferrocinepalladium (II) chloride (7.3 mg, 0.01 mmol). The mixture was then degassed using nitrogen for 10 min, and then heated (150° C.) in a microwave for 15 min. After cooling to room temperature, the mixture was diluted with methanol and concentrated under reduced pressure. The residue purified by silica gel chromatography using a 1 to 8% methanol/dichloromethane as the eluant to afford the desired product (5.9 mg, 11%). 1H-NMR (300 MHz, CD3OD) 7.86 (s, 1H), 7.81-7.87 (m, 4H), 7.73-7.79 (m, 2H), 7.63-7.69 (m, 1H), 7.53 (s, 1H), 7.40-7.49 (m, 2H), 7.22-7.28 (m, 2H), 3.92-3.99 (m, 2H), 2.38 (s, 3H); ES-MS m/z 558.3 (MH)+; HPLC RT (Method A) 2.64 min.

Workup

  1. customThe mixture was then degassed
  2. customfor 10 min
  3. temperatureAfter cooling to room temperature
  4. additionthe mixture was diluted with methanol
  5. concentrationconcentrated under reduced pressure
  6. customThe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-40e997600aa347e3b18f1740a6b98018
Source dataset
uspto-grants-2012_12
Patent number
US08338594B2

Reaction notes

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