Ethanol → HCID 9925329, compound

HRID 2215151Notes

Reaction equation

HRID 2215151 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:11]1[N:16]=[CH:15][C:14]([C:17]([N:19]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH2:23][N:22]3[CH:30]=[CH:31][CH:32]=[C:21]3[CH2:20]2)=[O:18])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+]>[C:1]1([C:11]2[N:16]=[CH:15][C:14]([C:17]([N:19]3[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[CH2:23][N:22]4[CH:30]=[CH:31][CH:32]=[C:21]4[CH2:20]3)=[O:18])=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 2194772510-[(6-Chloro-3-pyridinyl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 9925329HCID 9925329, compoundYield 27.5%

Reagents, catalysts & solvents 2

HCID 178476740HCID 178476740, compoundCatalystHCID 1140TolueneSolvent

Procedure

The title compound was prepared in the manner of Example 28 using phenylboronic acid (0.269 g), (6-chloro-pyridin-3-yl-[10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl]methanone of Example 28, Step A (0.645 g) and palladium(I) acetate (0.01 7g), in a mixture of toluene (1 2 mL), 1 M aqueous sodium carbonate (4 mL) and ethanol (2 mL). The initially obtained foam (0.387 g) was purified by HPLC (Primesphere C18, 5×25 cm column eluting with 55% acetonitrile in water containing 0.1% formic acid) to yield the title product (0.200 g) as a yellow solid. Recrystallization of a sample from acetone/hexane yielded yellow needles, m.p. 171–174° C.

Workup

  1. customThe initially obtained foam (0.387 g) was purified by HPLC (Primesphere C18, 5×25 cm column
  2. washeluting with 55% acetonitrile in water containing 0.1% formic acid)

Sources & evidence

ORD record
ord-1aa489aa6aaf43418e20ffaf8f27a811
Source dataset
uspto-grants-2006_09
Patent number
US07109193B2

Reaction notes

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