Dichloromethane → HCID 67255144, compound

HRID 2068295Notes

Reaction equation

HRID 2068295 reaction equation
ClCCl.[CH:4]1([NH:9][C:10]([C:12]2[CH:53]=[CH:52][C:15]3[N:16]([CH:38]4[CH2:43][CH2:42][CH:41]([O:44][Si:45]([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46])[CH2:40][CH2:39]4)[C:17]([NH:19][C:20]4[C:28]5[C:23](=[CH:24][CH:25]=[C:26](Br)[CH:27]=5)[N:22]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[N:21]=4)=[N:18][C:14]=3[CH:13]=2)=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5]1.[CH3:54][O:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O>[Si:45]([O:44][CH:41]1[CH2:40][CH2:39][CH:38]([N:16]2[C:15]3[CH:52]=[CH:53][C:12]([C:10]([NH:9][CH:4]4[CH2:5][CH2:6][CH2:7][CH2:8]4)=[O:11])=[CH:13][C:14]=3[N:18]=[C:17]2[NH:19][C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=4[O:55][CH3:54])[CH:27]=3)[N:22]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:36])([CH3:37])[CH3:35])[N:21]=2)[CH2:43][CH2:42]1)([C:48]([CH3:49])([CH3:50])[CH3:51])([CH3:47])[CH3:46]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 67252904HCID 67252904, compound

Product 1

HCID 67255144HCID 67255144, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of (1,1-Bis(diphenylphosphino)ferrocene)dichloropalladium(II), complexed with dichloromethane (1:1) (1.9 mg, 0.0000023 mol), 50 uL of 0.20 M 2-(5-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-3-ylamino)-1-(4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl)-1H-benzoimidazole-5-carboxylic acid cyclopentylamide (0.0000116 mol) in dioxane and 92 uL of 0.25 M 2-methoxyphenylboronic acid (3.54 mg, 0.0000233 mol) in dioxane and 29 uL 2.0 M sodium carbonate in water was heated at 120° C. for 4 hours. The reaction mixture was cooled, and 2 mL of H2O was added followed by extraction with 2 mL of methylene chloride 3 times. The combined organic phases were concentrated and purified by flash chromatography with 50% EtOAc/Hexanes to give the title compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionfollowed by extraction with 2 mL of methylene chloride 3 times
  3. concentrationThe combined organic phases were concentrated
  4. custompurified by flash chromatography with 50% EtOAc/Hexanes

Sources & evidence

ORD record
ord-b81f6c53447147f484d757a21e5f042f
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

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