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Water → HCID 70979338, compound

HRID 1485466
Notes
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Reaction equation

HRID 1485466 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][C@@H:13]([CH3:15])[C:12]3=[N:16][N:17]=[C:18]([CH3:19])[N:11]3[C:10]3[CH:20]=[CH:21][C:22](B4OC(C)(C)C(C)(C)O4)=[CH:23][C:9]2=3)=[CH:4][CH:3]=1.Br[C:34]1[CH:35]=[CH:36][C:37](=[O:41])[NH:38][C:39]=1[CH3:40].C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:14][C@@H:13]([CH3:15])[C:12]3=[N:16][N:17]=[C:18]([CH3:19])[N:11]3[C:10]3[CH:20]=[CH:21][C:22]([C:34]4[CH:35]=[CH:36][C:37](=[O:41])[NH:38][C:39]=4[CH3:40])=[CH:23][C:9]2=3)=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27344173-Bromo-6-hydroxy-2-methylpyridineHCID 70979017HCID 70979017, compound

Product 1

HCID 70979338HCID 70979338, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of (R)-6-(4-chlorophenyl)-1,4-dimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (100 mg, 0.22 mmol) in dioxane/water (11 mL, dioxane/water=10:1) was added 5-Bromo-6-methyl-1H-pyridin-2-one (51 mg, 0.27 mmol), cesium carbonate (145 mg, 0.44 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (17 mg, 0.022 mmol) under nitrogen atmosphere. The mixture was stirred and heated to reflux overnight. The mixture was cooled down and poured into water (30 mL) and extracted with ethyl acetate (20 ml×3). The combined organic phase was concentrated, and the residue was purified by HPLC (Mobile phase A: water with 0.05% ammonia solution; Mobile phase B: MeCN; column temperature: 30° C., Gradient: 25-55% B, 15 min) to give (R)-5-(6-(4-chlorophenyl)-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-8-yl)-6-methylpyridin-2(1H)-one as a white solid (16 mg, 17%).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. temperatureThe mixture was cooled down
  4. extractionextracted with ethyl acetate (20 ml×3)
  5. concentrationThe combined organic phase was concentrated
  6. customthe residue was purified by HPLC (Mobile phase A: water with 0.05% ammonia solution; Mobile phase B: MeCN; column temperature: 30° C., Gradient: 25-55% B, 15 min)

Sources & evidence

ORD record
ord-2c1800b85e944cd2ab8d79f782e64c29
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09422292B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes