Sodium hydride → HCID 67418218, compound

HRID 1429353Notes

Reaction equation

HRID 1429353 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH:13]([NH:21][S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32])(=[O:24])=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H-].[Na+].Br[CH2:36][C:37]1[CH:46]=[CH:45][CH:44]=[CH:43][C:38]=1[C:39]([O:41][CH3:42])=[O:40]>CN(C=O)C>[O:11]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[N:3]1[CH2:12][CH:13]([N:21]([CH2:36][C:37]1[CH:46]=[CH:45][CH:44]=[CH:43][C:38]=1[C:39]([O:41][CH3:42])=[O:40])[S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32])(=[O:24])=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 67417832HCID 67417832, compound

Product 1

HCID 67418218HCID 67418218, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of compound 2c (500 mg, 1.1 mmol) in DMF (10 mL) at 10° C., NaH (60 wt %, 44 mg, 1.1 mmol) was added in portions. The mixture was stirred for an additional 30 min and then the solution of methyl 2-(bromomethyl)-benzoate (253 mg, 1.1 mmol) in DMF (2 mL) was added dropwise. The resulting mixture was stirred at 10° C. for 30 min and warmed to rt overnight. The reaction was quenched with water and diluted with EA (40 mL), washed with brine (3×20 mL). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purification by silica gel flash chromatography (PE:EA=2:1) to give compound 2d as a white solid (520 mg, 79% yield).

Workup

  1. stirringThe resulting mixture was stirred at 10° C. for 30 min
  2. customThe reaction was quenched with water
  3. additiondiluted with EA (40 mL)
  4. washwashed with brine (3×20 mL)
  5. dry with materialThe organic phase was dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurification by silica gel flash chromatography (PE:EA=2:1)

Sources & evidence

ORD record
ord-578ed2cce06742698bd101b476e09d76
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

Loading…