Sodium hydride → HCID 58374670, compound

HRID 1482482Notes

Reaction equation

HRID 1482482 reaction equation
[H-].[Na+].[NH:3]1[CH2:8][CH2:7][O:6][CH2:5][C:4]1=[O:9].Br[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([B:18]2[O:22][C:21]([CH3:24])([CH3:23])[C:20]([CH3:26])([CH3:25])[O:19]2)=[CH:14][CH:13]=1>C(Cl)Cl>[CH3:23][C:21]1([CH3:24])[C:20]([CH3:25])([CH3:26])[O:19][B:18]([C:15]2[CH:14]=[CH:13][C:12]([CH2:11][N:3]3[CH2:8][CH2:7][O:6][CH2:5][C:4]3=[O:9])=[CH:17][CH:16]=2)[O:22]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 669533-MorpholinoneHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 58374670HCID 58374670, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

NaH (81 mg, 3 eq.) was added to a solution of morpholin-3-one in DCM. 2-(4-bromomethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane was added to the resulting solution and the reaction was stirred at room temperature for 16 hrs. DCM was evaporated, followed by addition of water. The solution was extracted with EtOAc. The organic layers were dried over MgSO4 and evaporated in vacuo to afford the title product used in the next step without further purification.

Workup

  1. customDCM was evaporated
  2. additionfollowed by addition of water
  3. extractionThe solution was extracted with EtOAc
  4. dry with materialThe organic layers were dried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-285a0e41ac75400686d6be93c267dcbb
Source dataset
uspto-grants-2016_08
Patent number
US09415037B2

Reaction notes

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