Dimethylformamide → HCID 67341483, compound

HRID 2092327Notes

Reaction equation

HRID 2092327 reaction equation
Br[C:2]1[C:10]2[C:5](=[C:6]([NH:11][C:12]3[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14](OC)[CH:13]=3)[N:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[CH3:24].[CH3:25][NH:26][C:27]1[N:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[C:32](B3OC(C)(C)C(C)(C)O3)[CH:33]=2)[N:28]=1.[C:46](=O)([O-])[O-:47].[Na+].[Na+].CN(C=O)C>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>[CH3:46][O:47][C:15]1[CH:14]=[CH:13][C:12]([NH:11][C:6]2[N:7]=[CH:8][CH:9]=[C:10]3[C:2]([C:32]4[CH:33]=[C:34]5[C:29](=[CH:30][CH:31]=4)[N:28]=[C:27]([NH:26][CH3:25])[N:36]=[CH:35]5)=[C:3]([CH3:24])[S:4][C:5]=23)=[CH:17][C:16]=1[C:18]([F:20])([F:21])[F:19]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 16086139N-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)quinazolin-2-amineHCID 67339438HCID 67339438, compound

Product 1

HCID 67341483HCID 67341483, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×

Conditions

Temperature
150 °C

Procedure

3-Bromo-N-(3-methoxy-5-(trifluoromethyl)phenyl)-2-methylthieno [2,3-c]pyridin-7-amine (0.230 g, 0.551 mmol), N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-2-amine (0.189 g, 0.661 mmol), dichlorobis(triphenyl-phosphine)palladium (II) (0.0193 g, 0.0276 mmol), sodium carbonate (0.117 g, 1.10 mmol) were all placed in a clear microwave vial along with 5 ml of 9:1 DMF:water. The vial was capped and heated in a Personal Chemistry SmithSynthesizer to 150° C. for 10 minutes. The reaction was diluted with water and extracted with EtAOc. The organic layer was washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel using a gradient of 50-100% EtOAc in hexanes. The pure fractions were reduced in vacuo and the residue triturated with ether to give 6-(7-(4-methoxy-3-(trifluoromethyl)phenylamino)-2-methylthieno[2,3-c]pyridin-3-yl)-N-methylquinazolin-2-amine as a yellow solid. MS (M+H)+ 496.

Workup

  1. customThe vial was capped
  2. extractionextracted with EtAOc
  3. washThe organic layer was washed (2×) with an aqueous saturated solution of sodium bicarbonate
  4. dry with materialThe organic layer was then dried with sodium sulfate
  5. custompurified by column chromatography on silica gel using a gradient of 50-100% EtOAc in hexanes
  6. customthe residue triturated with ether

Sources & evidence

ORD record
ord-eda76b40e576498cafcb93bcea35bd23
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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