Cesium carbonate → HCID 70979495, compound

HRID 1485386Notes

Reaction equation

HRID 1485386 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.[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:26]([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:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:9][C:6]=3[N:7]([CH3:26])[CH2:8][CH2:2][C:3]2=[N:15][N:14]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 86718493HCID 86718493, compound

Product 1

HCID 70979495HCID 70979495, compoundYield 41%

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), phenylboronic acid (42 mg, 0.34 mmol), tetrakis(triphenylphosphine)palladium (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 1,6-dimethyl-8-phenyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (20 mg, yield 41%).

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-799d77ff695849d58211fe62cee6e198
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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