Dichloromethane → HCID 178451734, compound

HRID 710170Notes

Reaction equation

HRID 710170 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[NH:16][C:15]2[CH:17]=[CH:18][C:19](B3OC(C)(C)C(C)(C)O3)=[CH:20][C:14]=2[N:13]=1.FC(F)(F)S(O[C:36]1[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH:37]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>CN(C=O)C.O.CCOC(C)=O.O>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[C:12]1[NH:16][C:15]2[CH:17]=[CH:18][C:19]([C:36]3[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH:37]=3)=[CH:20][C:14]=2[N:13]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 178431021HCID 178431021, compound

Product 1

HCID 178451734HCID 178451734, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
80 °C

Procedure

2-[2-fluoro-4-(methylsulfonyl)phenyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxa borolan-2-yl)-1H-benzo[d]imidazole (880 mg, 2.12 mmol), tert-butyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (700 mg, 2.12 mmol) and sodium carbonate (1.13 g, 11.48 mmol) were dissolved in DMF (20 ml) under N2 atmosphere. This mixture was degassed with nitrogen for 30 mins and added Pd(dppf)2Cl2.CH2Cl2 (138 mg, 0.17 mmol). This mixture stirred at 80° C. for 90 mins in microwave. Reaction mixture diluted with water and work up (AcOEt/H2O) afforded the crude. Crude was purified by combiflash using a mixture of AcOEt and Petether (35:65) to afford the titled compound (240 mg) as an off-white solid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 12.80 (s, 1H), 8.49 (t, J 7.5, 1H), 8.02 (d, J 10.4, 1H), 7.92 (d, J 8.2, 1H), 7.88-7.67 (m, 1H), 7.66-7.54 (m, 1H), 7.48-7.39 (m, 1H), 6.18 (bs, 1H), 4.02 (bs, 2H), 3.57 (bs, 2H), 3.34 (s, 3H), 2.60-2.55 (m, 2H), 1.43 (s, 9H).

Workup

  1. customThis mixture was degassed with nitrogen for 30 mins
  2. additionadded Pd(dppf)2Cl2
  3. customReaction mixture
  4. customafforded the crude
  5. customCrude was purified by combiflash
  6. additiona mixture of AcOEt and Petether (35:65)

Sources & evidence

ORD record
ord-f57cba79edef46c7aa9a862df9ae7852
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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