Cesium carbonate → HCID 71205429, compound

HRID 2280867Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[NH:12]1[CH2:15][CH:14]([OH:16])[CH2:13]1.C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[OH:16][CH:14]1[CH2:15][N:12]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=2)[C:7]([O:9][CH3:10])=[O:8])[CH2:13]1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of methyl 5-bromonicotinate (2.00 g, 9.26 mmol), azetidin-3-ol (1.01 g, 9.26 mmol), Cs2CO3 (9.06 g, 27.8 mmol), BINAP (1.15 g, 1.85 mmol) and Pd(OAc)2 (0.44 g, 1.85 mmol) in dry dioxane (115 mL) was heated overnight at 85° C. under N2 atmosphere. The resulting mixture was filtrated, concentrated under reduced pressure and purified by prep-HPLC to give compound 11a (250 mg, 13%) of as a yellow solid.

Workup

filtrationThe resulting mixture was filtrated
concentrationconcentrated under reduced pressure
custompurified by prep-HPLC

Sources & evidence

ORD record: ord-a68232a4c65b43f0bab25d60f382bf99
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139539B2

Reaction notes

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