Dichloromethane → HCID 86727396, compound

HRID 519034Notes

Reaction equation

HRID 519034 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][C:32]1(C)[C:36](C)(C)OB(C(C)=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[C:32]([CH3:36])=[CH2:31])[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 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 86727397HCID 86727397, compound

Product 1

HCID 86727396HCID 86727396, compoundYield 75%

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 (0.080 g, 0.166 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (0.084 g, 0.499 mmol), K2CO3 (0.046 g, 0.332 mmol) and Pd(dppf)Cl2.CH2Cl2 (0.014 g, 0.017 mmol) in dioxane (3 mL) and H2O (0.5 mL) was stirred at 90° C. for 15 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-(7-isopropenyl-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 as a white solid (0.055 g, 75%). LC/MS (Table 1, Method 2) Rt=1.240 min.; MS m/z: 443 [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-6b85e694bec14aea8fb5ec9ff0021ed0
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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