Dichloromethane → HCID 178434533, compound

HRID 1530552Notes

Reaction equation

HRID 1530552 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][N:11]3[C:7](=[N:8][C:9](I)=[CH:10]3)[C:6]=2[CH:16]=1.[CH3:17][C:18]1[C:22](B2OC(C)(C)C(C)(C)O2)=[CH:21][NH:20][N:19]=1.C(Cl)Cl.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][N:11]3[C:7](=[N:8][C:9]([C:22]4[C:18]([CH3:17])=[N:19][NH:20][CH:21]=4)=[CH:10]3)[C:6]=2[CH:16]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 5820440710-Bromo-2-iodo-5,6-dihydrobenzo[F]imidazo[1,2-D][1,4]oxazepineHCID 178434487HCID 178434487, compound

Product 1

HCID 178434533HCID 178434533, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 9-bromo-2-iodo-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (200 mg, 0.51 mmol), 3-methylpyrazole-4-boronic acid pinacol ester (117 mg, 0.56 mmol), PdCl2dppf.DCM (42 mg, 0.05 mmol) and Cs2CO3 (416 mg, 1.28 mmol) in dioxane (4 mL) and H2O (1 mL) was purged with argon and heated at 80° C. for 1 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-3% MeOH in DCM) affording 9-Bromo-2-(3-methyl-1H-pyrazol-4-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (53 mg, 30%). LCMS: RT 2.21 min [M+H]+ 345.3

Workup

  1. washwas washed with MeOH
  2. washthe product eluted with 2M NH3/MeOH
  3. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 0-3% MeOH in DCM)

Sources & evidence

ORD record
ord-51e535c6ab98407d8c384f9c1d46cc06
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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