Dichloromethane → HCID 86727401, compound

HRID 519037Notes

Reaction equation

HRID 519037 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([O:13][C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2Br)[O:24][CH2:23][C:22]2[N:17]3[CH:18]([CH3:30])[C:19](=[O:29])[NH:20][N:21]=2)([CH3:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:31]B1OB(C)OB(C)O1.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][C:10]([O:13][C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2[CH3:31])[O:24][CH2:23][C:22]2[N:17]3[CH:18]([CH3:30])[C:19](=[O:29])[NH:20][N:21]=2)([CH3:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 86727397HCID 86727397, compound

Product 1

HCID 86727401HCID 86727401, compoundYield 87.3%

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)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (Example #82, Step A, 0.032 g, 0.066 mmol), 2,4,6-trimethyl-cyclotriboroxane (0.025 g, 0.199 mmol), K2CO3 (0.018 g, 0.133 mmol) and Pd(dppf)Cl2.CH2Cl2 (0.006 g, 0.007 mmol) in dioxane (3 mL) and water (0.5 mL) was stirred at 110° C. for 4 h. The solvent was removed in vacuo and the residue was purified by preparative TLC (eluting with 30% EtOAc in petroleum ether) to give 3-(4,7-dimethyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yloxy)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester as a white solid (0.024 g, 87%). LC/MS (Table 1, Method 2) Rt=1.160 min.; MS m/z: 417 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by preparative TLC (eluting with 30% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-c68eeff6c5ab426c8357cad62891aff9
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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