HCID 67060825, compound → HCID 70664288, compound

HRID 1186081Notes

Reaction equation

HRID 1186081 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:16]2[CH:17]=[C:18](B3OC(C)(C)C(C)(C)O3)[CH:19]=[CH:20][C:15]=2[NH:14][C:13]1=[O:30])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl[C:32]1[C:33]2[CH:60]=[C:59]([Cl:61])[CH:58]=[CH:57][C:34]=2[N:35]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=2)[C:36](=[O:47])[C@H:37]([CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[Cl:46])[N:38]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.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>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:16]2[CH:17]=[C:18]([C:32]3[C:33]4[CH:60]=[C:59]([Cl:61])[CH:58]=[CH:57][C:34]=4[N:35]([CH2:48][C:49]4[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=4)[C:36](=[O:47])[C@H:37]([CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=4[Cl:46])[N:38]=3)[CH:19]=[CH:20][C:15]=2[NH:14][C:13]1=[O:30])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 67060825HCID 67060825, compoundHCID 67060837HCID 67060837, compound

Product 1

HCID 70664288HCID 70664288, compoundYield 12.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

1-(3-((Tert-Butyldimethylsilyl)oxy)propyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one (0.46 g, 1.06 mmol) and (S)-5,7-dichloro-3-(2-chlorobenzyl)-1-(4-methoxybenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (0.5 g, 1.06 mmol) were combined in toluene (4 mL) and saturated aqueous sodium bicarbonate (2 mL) and purged with nitrogen. Tetrakis(triphenylphosphine)palladium (122 mg, 0.106 mmol) was added and the mixture was heated at 90° C. for 7.5 h. After cooling, the mixture was diluted with ethyl acetate and washed twice with water then once with brine then dried (MgSO4). Chromatography, eluting with 10-50% ethyl acetate in hexanes gave the title compound as an orange brown solid (100 mg, 0.134 mmol).

Workup

  1. customsaturated aqueous sodium bicarbonate (2 mL) and purged with nitrogen
  2. temperatureAfter cooling
  3. washwashed twice with water
  4. dry with materialonce with brine then dried (MgSO4)
  5. washChromatography, eluting with 10-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-90c9929d567745e5886d9579d017c818
Source dataset
uspto-grants-2014_03
Patent number
US08673897B2

Reaction notes

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