Dimethylformamide → HCID 117675490, compound

HRID 1526186Notes

Reaction equation

HRID 1526186 reaction equation
Br[C:2]1[CH:34]=[CH:33][C:5]([O:6][C:7]2[N:12]=[C:11]([O:13][C:14]3[CH:15]=[C:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:17]=[CH:18][CH:19]=3)[C:10]([CH2:28][CH3:29])=[N:9][C:8]=2[C:30](=[O:32])[NH2:31])=[CH:4][CH:3]=1.[CH3:35][N:36]1[CH2:41][CH:40]=[C:39](B2OC(C)(C)C(C)(C)O2)[CH2:38][CH2:37]1.CN(C)C=O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C>[C:30]([C:8]1[N:9]=[C:10]([CH2:28][CH3:29])[C:11]([O:13][C:14]2[CH:15]=[C:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:17]=[CH:18][CH:19]=2)=[N:12][C:7]=1[O:6][C:5]1[CH:33]=[CH:34][C:2]([C:39]2[CH2:40][CH2:41][N:36]([CH3:35])[CH2:37][CH:38]=2)=[CH:3][CH:4]=1)(=[O:32])[NH2:31]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 207733711-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridineHCID 117675489HCID 117675489, compound

Product 1

HCID 117675490HCID 117675490, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of tert-butyl (3-{[6-(4-bromophenoxy)-5-carbamoyl-3-ethylpyrazin-2-yl]oxy}phenyl)carbamate (540 mg), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine (273 mg), and N,N-dimethylformamide (10 mL) were added a 1,1′-bis(diphenylphosphino)ferrocene palladium (II) dichloride-dichloromethane complex (83 mg) and cesium carbonate (665 mg), followed by reacting at 80° C. for 1 hour. The reaction mixture was left to be cooled, and then ethyl acetate was added thereto. The mixture was washed with water and saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=1:0-9:1) and silica gel column chromatography (NH2 type, eluent; chloroform:methanol=100:0-98:2) to obtain tert-butyl [3-({5-carbamoyl-3-ethyl-6-[4-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)phenoxy]pyrazin-2-yl}oxy)phenyl]carbamate (153 mg) as a pale yellow oily substance.

Workup

  1. waitThe reaction mixture was left
  2. temperatureto be cooled
  3. washThe mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=1:0-9:1) and silica gel column chromatography (NH2 type, eluent; chloroform:methanol=100:0-98:2)

Sources & evidence

ORD record
ord-f58dff83c3a2483fb9ee9de03088c37b
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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