Dichloromethane → HCID 71090334, compound

HRID 710172Notes

Reaction equation

HRID 710172 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[O:13][C:14]2[CH:20]=[CH:19][C:18](B3OC(C)(C)C(C)(C)O3)=[CH:17][C:15]=2[N:16]=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[O:13][C:14]2[CH:20]=[CH:19][C:18]([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:17][C:15]=2[N:16]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 71257308HCID 71257308, compound

Product 1

HCID 71090334HCID 71090334, compoundYield 44.1%

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)benzo[d]oxazole (50 mg, 0.12 mmol), tert-butyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (39 mg, 0.12 mmol) and sodium carbonate (38 mg, 0.36 mmol) were dissolved in DMF (2 ml) under N2 atmosphere. This mixture was degassed with nitrogen for 30 mins and added Pd(dppf)2Cl2.CH2Cl2 (10 mg, 0.009 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 (27:73) to afford the titled compound (25 mg) as an off-white solid. M.P.: 149-151° C. 1H-NMR (δ ppm, CDCl3, 400 MHz): 8.47 (t, J 7.4, 1H), 7.93-7.80 (m, 3H), 7.65-7.57 (m, 1H), 7.53-7.45 (m, 1H), 6.20-6.02 (m, 1H), 4.12 (bs, 2H), 3.68 (t, J 5.3, 2H), 3.13 (s, 3H), 2.65-2.55 (m, 2H), 1.50 (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 (27:73)

Sources & evidence

ORD record
ord-179c40a2f50f4c53aed644f8a08a4c31
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

Loading…