Dichloromethane → HCID 86727352, compound

HRID 518997Notes

Reaction equation

HRID 518997 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:14]=[C:15]3[C:24](=[CH:25][C:26]=2Br)[O:23][CH2:22][C:21]2[N:16]3[CH:17]([CH3:29])[C:18](=[O:28])[NH:19][N:20]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:30](B(O)O)([CH3:32])=[CH2:31].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>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]>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:14]=[C:15]3[C:24](=[CH:25][C:26]=2[C:30]([CH3:32])=[CH2:31])[O:23][CH2:22][C:21]2[N:16]3[CH:17]([CH3:29])[C:18](=[O:28])[NH:19][N:20]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 10855372(Prop-1-en-2-yl)boronic acidHCID 86727349HCID 86727349, compound

Product 1

HCID 86727352HCID 86727352, compoundYield 328.2%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-(7-bromo-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-azetidine-1-carboxylic acid tert-butyl ester (Example #65, Step G, 0.030 g, 0.064 mmol), isopropenyl boronic acid (0.032 g, 0.193 mmol), K2CO3 (0.018 g, 0.13 mmol) and Pd(dppf)Cl2.CH2Cl2 (0.011 g, 0.013 mmol) in dioxane (3 mL) and H2O (0.5 mL) was stirred at 80° C. for 15 h. The mixture was cooled to ambient temperature and the solvent was removed in vacuo. The residue was purified by preparative TLC (eluting with 20% EtOAc in petroleum ether) to give 3-(7-isopropenyl-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-azetidine-1-carboxylic acid tert-butyl ester as a white solid (0.09 g, 33%). LC/MS (Table 1, Method 2) Rt=1.241 min.; MS m/z: 429 [M+H]+.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by preparative TLC (eluting with 20% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-e91c0a37a2874e33b2cfa9948331db82
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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