Tetrahydrofuran → HCID 70979095, compound

HRID 1485445Notes

Reaction equation

HRID 1485445 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([CH3:15])=[N:13][N:14]=[C:10]3[CH:9]([CH3:16])[CH2:8][N:7]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[C:6]=2[CH:25]=1.CC1(C)C(C)(C)OB([C:34]2[CH:35]=[CH:36][C:37]([NH2:40])=[N:38][CH:39]=2)O1.C(=O)([O-])[O-].[K+].[K+].O1CCCC1>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[NH2:40][C:37]1[N:38]=[CH:39][C:34]([C:2]2[CH:3]=[CH:4][C:5]3[N:11]4[C:12]([CH3:15])=[N:13][N:14]=[C:10]4[CH:9]([CH3:16])[CH2:8][N:7]([C:17]4[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=4)[C:6]=3[CH:25]=2)=[CH:35][CH:36]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 70978960HCID 70978960, compound

Product 1

HCID 70979095HCID 70979095, compoundYield 59.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(8-bromo-1,4-dimethyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-6(5H)-yl)benzonitrile (244 mg, 0.62 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (274 mg, 1.24 mmol), tetrakis(triphenylphosphine)palladium(0) (50 mg) and potassium carbonate (350 mg, 2.53 mmol) in a mixed solution of tetrahydrofuran (10 mL) and water (1 mL) was heated at 100° C. for 30 minutes under microwave (pressure: 17.2 bar, equipment power: 150 W). The reaction mixture was diluted with ethyl acetate (20 mL) and washed with brine (10 mL*3). The organic phase was separated, dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated to give a crude product, which was purified by column chromatography (silica gel, dichloromethane/methanol=12:1) to afford 4-(8-(6-aminopyridin-3-yl)-1,4-dimethyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-6(5H)-yl)benzonitrile as a light yellow solid (150 mg, 59.4%). LRMS (M+H)+: calcd 407.19. found 407.

Workup

  1. washwashed with brine (10 mL*3)
  2. customThe organic phase was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customto give a crude product, which
  7. customwas purified by column chromatography (silica gel, dichloromethane/methanol=12:1)

Sources & evidence

ORD record
ord-8ba82f42ca664cdcb592102572972f8f
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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