4-Aminocarbonylphenylboronic acid → HCID 68084725, compound

HRID 1047087Notes

Reaction equation

HRID 1047087 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[NH:19][C:18]4[N:26]=[CH:27][CH:28]=[CH:29][C:17]=4[N:16]3[C:30]=2[C:31]2[CH:36]=[CH:35][C:34]([C:37]3([NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:40][CH2:39][CH2:38]3)=[CH:33][CH:32]=2)=[CH:9][CH:8]=1)(=O)=O.[NH2:51][C:52]([C:54]1[CH:59]=[CH:58][C:57](B(O)O)=[CH:56][CH:55]=1)=[O:53]>C1(C)C=CC=CC=1.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:52]([C:54]1[CH:59]=[CH:58][C:57]([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[N:14]=[C:15]4[C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=5[NH:19][C:18]5[N:26]=[CH:27][CH:28]=[CH:29][C:17]=5[N:16]4[C:30]=3[C:31]3[CH:32]=[CH:33][C:34]([C:37]4([NH:41][C:42](=[O:43])[O:44][C:45]([CH3:47])([CH3:46])[CH3:48])[CH2:38][CH2:39][CH2:40]4)=[CH:35][CH:36]=3)=[CH:11][CH:12]=2)=[CH:56][CH:55]=1)(=[O:53])[NH2:51]

Participants

6

Reactant 2

HCID 27378114-Aminocarbonylphenylboronic acidHCID 86664676HCID 86664676, compound

Product 1

HCID 68084725HCID 68084725, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-[3-(4-{1-[(tert-butoxycarbonyl)amino]cyclobutyl}phenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-2-yl]phenyl trifluoromethanesulfonate (30 mg, 0.043 mmol) in toluene (1 mL) and EtOH (1 mL) was added saturated 1M-K3PO4aq, 4-aminocarbonylphenylboronic acid (21 mg, 0.13 mmol) and Pd (PPh3)4 (5 mg, 0.0043 mmol). The reaction was degassed for 2 minutes and then heated at 100° C., 2.5 h. The reaction mixture was cooled to room temperature, then was diluted with EtOAc (15 mL) and washed with brine. The organic phase was dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (SiO2, 20% to 50% to 100% EtOAc in hexane) gave the title compound as a white solid (22 mg, 76%); LCMS: 675 [M+H].

Workup

  1. customThe reaction was degassed for 2 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additionwas diluted with EtOAc (15 mL)
  4. washwashed with brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography (SiO2, 20% to 50% to 100% EtOAc in hexane)

Sources & evidence

ORD record
ord-3965ae765b0a41088f4ab145bfa5a4f6
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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