Toluene → HCID 60166991, compound

HRID 473503Notes

Reaction equation

HRID 473503 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[C:21]3[CH2:20][CH2:19][C:18]4[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=4[C:16](=[O:26])[C:15]=3[CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:27][C:28]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:29]=1[NH2:30].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C1(C)C=CC=CC=1>CC([O-])=O.CC([O-])=O.[Pd+2].C(O)(C)(C)C>[F:27][C:28]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:29]=1[NH:30][C:23]1[CH:24]=[CH:25][C:17]2[C:16](=[O:26])[C:15]3[CH:21]=[C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)[CH:12]=[CH:13][C:14]=3[CH2:20][CH2:19][C:18]=2[CH:22]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 97092,4-DifluoroanilineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86664812HCID 86664812, compound

Product 1

HCID 60166991HCID 60166991, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6386tert-ButanolSolvent

Procedure

In accordance with general method AA, 0.67 g (1.8 mmol) of 2-chloro-7-(3-morpholin-4-yl-propoxy-10,11-dihydrodibenzo[a,d]-cyclohepten-5-one (36i), 0.25 g (1.9 mmol) of 2,4-difluoroaniline, 0.05 g (0.22 mmol) of Pd(OAc)2, 0.10 g (0.21 mmol) of 2-(dicyclohexylphosphino)-2′-,4′-,6′-triisopropyl-biphenyl, 0.60 g (6.2 mmol) of Na—O-tert-butylate, 5 ml of toluene and 1 ml of tert-BuOH are used. Reaction time: 1 h. Purification is carried out via flash chromatography (SiO2, hexane/ethyl acetate 7+3). C28H28F2N2O3 (Mr=478.54); yield 43%; m.p. 114° C.

Workup

  1. customReaction time
  2. custom1 h
  3. customPurification

Sources & evidence

ORD record
ord-7a3b6ab86c514e0db453ebb4a7fc5c16
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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