Ethyl Acetate → HCID 178510018, compound

HRID 1625209Notes

Reaction equation

Br[C:2]1[CH:9]=[C:8]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][C:18]([C:19]4[CH:20]=[N:21][C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[C:13]3[C:12]([C:29]([F:32])([F:31])[F:30])=[N:11]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[OH:33][C@H:34]1[CH2:39][CH2:38][C@H:37]([NH2:40])[CH2:36][CH2:35]1.CC(C)([O-])C.[Na+].C(OCC)(=O)C>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[OH:33][C@H:34]1[CH2:39][CH2:38][C@H:37]([NH:40][C:2]2[CH:9]=[C:8]([N:10]3[C:14]4=[N:15][CH:16]=[CH:17][C:18]([C:19]5[CH:20]=[N:21][C:22]6[C:27]([CH:28]=5)=[CH:26][CH:25]=[CH:24][CH:23]=6)=[C:13]4[C:12]([C:29]([F:32])([F:31])[F:30])=[N:11]3)[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:36][CH2:35]1

Participants

Conditions

Temperature: 140 °C

Procedure

A solution of a mixture of compound (1e) (0.560 g), trans-4-hydroxycyclohexylamine (0.522 g), sodium tert-butoxide (0.218 g), palladium acetate (0.025 g), and 1,1-bis-(diphenylphosphino)-ferrocene (0.126 g) in 1,4-dioxane (12 mL) was stirred under a nitrogen atmosphere at 140° C. for 2 hr. The reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with saturated saline. The organic layer after the washing was dried over anhydrous sodium sulfate, and then the solvent was distilled away. The residue was purified by neutral silica gel column chromatography (chloroform/methanol) to obtain compound (1f) (0.450 g, 75%) as a white solid.

Workup

washthe organic layer was washed with saturated saline
dry with materialThe organic layer after the washing was dried over anhydrous sodium sulfate
distillationthe solvent was distilled away
customThe residue was purified by neutral silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record: ord-2d602320785e4b16aa7153baf717d1bd
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08779142B2

Reaction notes

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