Binap, (A+-)- → HCID 69732686, compound

HRID 2182148Notes

Reaction equation

[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[N:12][C:11](Br)=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:25][C:26]([CH3:29])([O-:28])[CH3:27].[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=[CH:75][CH:76]=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[C:26]([O:28][C:6]([N:7]1[CH2:76][CH2:75][N:12]([C:11]2[CH:10]=[N:9][C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:24])=[C:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=3)[N:12]=2)[CH2:13][CH2:8]1)=[O:5])([CH3:29])([CH3:27])[CH3:25]

Participants

Conditions

Temperature: 80 °C

Procedure

[5-Bromo-3-(3-chloro-benzyloxy)-pyrazin-2-yl]-carbamic acid tert-butyl ester I-3p (2.18 g, 5.3 mmol), pperazine-1-carboxylic acid tert-butyl ester (1.18 g, 6.3 mmol), sodium tert-butoxide (0.71 g, 7.4 mmol), racemic BINAP (196 mg, 315 μmol), and tris(benzylideneacetone)dipalladium (96.5 mg, 105 μmol) were placed in a vial equipped with a septum cap. The vial was evacuated and backfilled with dry nitrogen three times, and toluene (11 mL) added. The mixture was heated to 80° C. for 2 h then cooled to room temperature. Resulting suspension was transferred to a flask with CH2Cl2 and concentrated in vacuo to an amber oily solid. Purification by silica gel column (hexanes/EtOAc 7:3) gave the title compound I-3q as a yellow foam (560 mg, 25% yield).

Workup

customa vial equipped with a septum
customcap
customThe vial was evacuated
additionadded
temperaturethen cooled to room temperature
customResulting suspension
concentrationconcentrated in vacuo to an amber oily solid
customPurification by silica gel column (hexanes/EtOAc 7:3)

Sources & evidence

ORD record: ord-c2ea1b270f7e41bc9c936d70cee86767
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06894050B2

Reaction notes

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