Cesium carbonate → HCID 70979073, compound

HRID 1485387Notes

Reaction equation

HRID 1485387 reaction equation
Br[CH:2]1[CH2:8][NH:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]2[C:13]([CH3:16])=[N:14][N:15]=[C:3]12.CC1(C)C(C)(C)OB([C:25]2[CH:26]=[CH:27][C:28]([NH2:31])=[N:29][CH:30]=2)O1.[C:33]([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.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>[CH3:16][C:13]1[N:4]2[C:5]3[CH:12]=[CH:11][C:10]([C:25]4[CH:26]=[CH:27][C:28]([NH2:31])=[N:29][CH:30]=4)=[CH:9][C:6]=3[N:7]([CH3:33])[CH2:8][CH2:2][C:3]2=[N:15][N:14]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 86718493HCID 86718493, compound

Product 1

HCID 70979073HCID 70979073, compoundYield 38.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of bromo-1-methyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (50 mg, 0.17 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (75 mg, 0.34 mmol), Tetrakis(triphenylphosphine)palladium(0)(10 mg) and Cs2CO3 (110 mg, 0.34 mmol) in dioxane (5 mL) and water (1 mL) was heated at 120° C. under microwave for 20 min. The reaction mixture was concentrated to give the crude product, which was purified by prep-TLC (DCM:MeOH=10:1) to afford 5-(1,6-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-8-yl)pyridin-2-amine (20 mg, yield 38%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give the crude product, which
  3. customwas purified by prep-TLC (DCM:MeOH=10:1)

Sources & evidence

ORD record
ord-9f8b8433d233441f9823c41c797afb7c
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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