1,2-Dimethoxyethane → HCID 117602003, compound

HRID 1773693Notes

Reaction equation

HRID 1773693 reaction equation
[CH2:1]([O:3][C:4]1[NH:8][C:7]2[CH:9]=[C:10]([C:14]3[C:15]([CH3:20])=[N:16][O:17][C:18]=3[CH3:19])[CH:11]=[C:12](I)[C:6]=2[N:5]=1)[CH3:2].[CH3:21][N:22]1[C:26](B2OC(C)(C)C(C)(C)O2)=[C:25]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:24]=[N:23]1.COCCOC>O>[CH2:1]([O:3][C:4]1[NH:8][C:7]2[CH:9]=[C:10]([C:14]3[C:15]([CH3:20])=[N:16][O:17][C:18]=3[CH3:19])[CH:11]=[C:12]([C:26]3[N:22]([CH3:21])[N:23]=[CH:24][C:25]=3[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:6]=2[N:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 117601989HCID 117601989, compoundHCID 123172170HCID 123172170, compound

Product 1

HCID 117602003HCID 117602003, compoundYield 14.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

4-(2-ethoxy-4-iodo-1H-benzo[d]imidazol-6-yl)-3,5-dimethylisoxazole (100 mg, 0.26 mmol) and 1-methyl-4-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (37 mg, 0.13 mmol) was added to a solvent mixture of 1,2-dimethoxyethane (2 ml) and water (1 ml). To the above mixture were added PEPPSI-Ipr (18 mg, 0.026 mmol) and CsCO3 (127 mg, 0.39 mmol). The reaction mixture was heated at 130° C. in microwave reactor for 30 mins. The reaction mixture was then filtered and organic solvent was evaporated and the residue was purified with Prep HPLC (0-100% CH3CN/H2O) to afford 8 mg product 4-(2-ethoxy-4-(1-methyl-4-phenyl-1H-pyrazol-5-yl)-1H-benzo[d]imidazol-6-yl)-3,5-dimethylisoxazole.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customorganic solvent was evaporated
  3. customthe residue was purified with Prep HPLC (0-100% CH3CN/H2O)

Sources & evidence

ORD record
ord-b71ebfae2bb5473087e5fbea24e542fb
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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