2-(Di-tert-butylphosphino)biphenyl → HCID 86689019, compound

HRID 40518Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11](=[O:15])[N:12]([CH3:14])[CH3:13])[CH3:9])=[CH:4][CH:3]=1.[CH2:16]([O:18][C:19]1[CH:29]=[CH:28][C:22]([O:23][CH:24]2[CH2:27][NH:26][CH2:25]2)=[C:21]([F:30])[CH:20]=1)[CH3:17].CC([O-])(C)C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CO.O>[CH2:16]([O:18][C:19]1[CH:29]=[CH:28][C:22]([O:23][CH:24]2[CH2:25][N:26]([C:2]3[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11](=[O:15])[N:12]([CH3:14])[CH3:13])[CH3:9])=[CH:4][CH:3]=3)[CH2:27]2)=[C:21]([F:30])[CH:20]=1)[CH3:17]

Participants

Conditions

Temperature: 80 °C

Procedure

Under an argon atmosphere a mixture of 0.080 g (0.295 mmol) (S)-3-[1-(4-bromo-phenyl)-ethyl]-1,1-dimethyl-urea (II.1), 0.073 g (0.295 mmol) 3-(4-ethoxy-2-fluoro-phenoxy)-azetidine (IX.2), 0.117 g (97%, 1.18 mmol) NaOtBu, 0.0035 g (0.118 mmol) 2-(di-tert-butylphosphino)biphenyl, 0.027 g (0.0295 mmol) tris-(dibenzylideneaceton)-dipalladium(0) in 1.5 mL 1,4-dioxane is stirred for 3 h at 80° C. Few water and methanol is added, the mixture is filtered and concentrated in vacuo. The residue is purified by HPLC (GeminiC18, methanol/water (+0.3% NH4OH)) to yield the desired product.

Workup

filtrationthe mixture is filtered
concentrationconcentrated in vacuo
customThe residue is purified by HPLC (GeminiC18, methanol/water (+0.3% NH4OH))

Sources & evidence

ORD record: ord-594b3b0544c2419a86b30f01cde02216
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530461B2

Reaction notes

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