Nitrogen → HCID 57539290, compound

HRID 1715520Notes

Reaction equation

HRID 1715520 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][CH:3]=1.[C:13]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].N#N.CC(C)([O-])C.[Na+].ClP(C(C)(C)C)C(C)(C)C>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:13]([C:17]1[CH:22]=[CH:21][C:20]([N:23]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]3[O:12][CH2:11][CH2:10][O:9]3)=[CH:4][CH:3]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

8

Reactant 5

HCID 947NitrogenHCID 139566Di-tert-butylchlorophosphineHCID 27738422-(4-Bromophenyl)-1,3-dioxolaneHCID 11447459(4-tert-Butyl-phenyl)-phenyl-amineHCID 23676156Sodium t-butoxide

Product 1

HCID 57539290HCID 57539290, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

48.8 g (213 mmol) of 2-(4-bromophenyl)-1,3-dioxolane and 48 g (213 mmol) of (4-tert-butylphenyl)phenylamine are initially introduced in 750 ml of toluene, and the solution is saturated with N2 for about 30 min. 29.2 g (304 mmol) of sodium tert-butoxide are subsequently added in small portions, followed by 760 mg (4.2 mmol) of chlorobis-t-butylphosphine and 485 mg (2.1 mmol) of Pd(OAc)2. The mixture is refluxed for 3 h with monitoring by TLC.

Workup

  1. temperatureThe mixture is refluxed for 3 h with monitoring by TLC

Sources & evidence

ORD record
ord-781e685e02d04d64bfe036c7f50e2677
Source dataset
uspto-grants-2010_09
Patent number
US07799875B2

Reaction notes

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