Nitrogen → HCID 67974825, compound

HRID 1771465Notes

Reaction equation

HRID 1771465 reaction equation
[CH3:1][Mg]Cl.N#N.[CH2:6]([O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1)[C:18](OS(C(F)(F)F)(=O)=O)=[CH:17]2)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1COCC1.[Cl-].[Cl-].[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:6]([O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1)[C:18]([CH3:1])=[CH:17]2)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 947NitrogenHCID 86698071HCID 86698071, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 67974825HCID 67974825, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ZnCl2 (1.32 g, 9.68 mmol) in anhydrous THF (20 mL) was added MeMgCl (1.6 mL, 4.80 mmol, 3M in THF) and the mixture was stirred at under N2 atmosphere at 10° C. for 1 hour. Then methyl 4-(6-(benzyloxy)-3-(((trifluoromethyl)sulfonyl)oxy)naphthalen-2-yl)benzoate (500 mg, 0.968 mmol) and Pd(PPh3)4 (100 mg, 0.0865 mmol) was added and the mixture was stirred at 60° C. under N2 atmosphere for 3 hours. After an aqueous/EtOAc workup, the residue was purified by silica gel column (PE/EtOAc=40/1) to give the product (250 mg, yield 68%) as an off-white solid.

Workup

  1. customAfter an aqueous/EtOAc workup, the residue was purified by silica gel column (PE/EtOAc=40/1)

Sources & evidence

ORD record
ord-70f8d412a96f4d43b447eb4bbfa811f8
Source dataset
uspto-grants-2016_02
Patent number
US09249132B2

Reaction notes

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