2-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl → HCID 67285789, compound

HRID 1618793Notes

Reaction equation

CC(C)([O-])C.[Na+].CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C.Cl[C:41]1[C:50]2[C:45](=[CH:46][C:47]([F:51])=[CH:48][CH:49]=2)[N:44]=[C:43]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][N:53]=2)[C:42]=1[CH3:58].[CH3:59][C:60]1([CH3:80])[O:79][CH2:78][C:63]2([C:71]3[C:66](=[CH:67][C:68]([N:72]4[CH2:77][CH2:76][O:75][CH2:74][CH2:73]4)=[CH:69][CH:70]=3)[NH:65][CH2:64]2)[CH2:62][O:61]1>CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C1(C)C=CC=CC=1>[F:51][C:47]1[CH:46]=[C:45]2[C:50]([C:41]([N:65]3[C:66]4[C:71](=[CH:70][CH:69]=[C:68]([N:72]5[CH2:77][CH2:76][O:75][CH2:74][CH2:73]5)[CH:67]=4)[C:63]4([CH2:62][O:61][C:60]([CH3:80])([CH3:59])[O:79][CH2:78]4)[CH2:64]3)=[C:42]([CH3:58])[C:43]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][N:53]=3)=[N:44]2)=[CH:49][CH:48]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a microwave vial was added sodium tert-butoxide (0.035 g, 0.37 mmol), ruphos (8.6 mg, 0.018 mmol), 4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)-quinoline (0.053 g, 0.19 mmol), 2,2-dimethyl-6′-morpholinospiro[[1,3]dioxane-5,3′-indoline] (0.056 g, 0.18 mmol), and XPhos pre-catalyst (0.014 g, 0.018 mmol) in toluene (1.2 mL). The suspension was deoxygenated with argon for 5 min and stirred at 100° C. for 90 min under microwave irradiation. Purification by column chromatography (eluting with a gradient of 10-60% EtOAc in hexanes) gave 1′-(7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yl)-2,2-dimethyl-6′-morpholinospiro[[1,3]dioxane-5,3′-indoline] as a yellow solid. Mass Spectrum (ESI) m/e=541.3 (M+1).

Workup

customThe suspension was deoxygenated with argon for 5 min
customPurification by column chromatography (
washeluting with a gradient of 10-60% EtOAc in hexanes)

Sources & evidence

ORD record: ord-7a42c9cf74934b40819d438aed102e3b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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