HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium hydride → HCID 59682304, compound

HRID 1714251
Notes
Print preview

Reaction equation

HRID 1714251 reaction equation
[H-].[Na+].ClC1C2N=C(CC(F)(F)F)[N:9](Cl)C=2C=CC=1.[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][C:28]=1[Cl:29])[NH:25][C:24]([CH2:30][C:31]([F:34])([F:33])[F:32])=C2.Br[CH2:36][C:37]1[CH:42]=[CH:41][C:40]([N:43]2[CH:47]=[CH:46][CH:45]=[CH:44]2)=[CH:39][CH:38]=1.[NH4+].[Cl-]>CN(C=O)C>[Cl:29][C:28]1[C:20]([Cl:19])=[CH:21][C:22]2[N:9]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([N:43]4[CH:47]=[CH:46][CH:45]=[CH:44]4)=[CH:39][CH:38]=3)[C:24]([CH2:30][C:31]([F:32])([F:33])[F:34])=[N:25][C:26]=2[CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27954561-[4-(Bromomethyl)phenyl]-1H-pyrroleHCID 669688335,6-Dichloro-2-(2,2,2-trifluoro-ethyl)-1H-indoleHCID 66968977dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzoimidazole

Product 1

HCID 59682304
HCID 59682304, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

NaH (60%) (60 mg, 1.5 mmol) was added into a solution of dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzoimidazole. 5,6-Dichloro-2-(2,2,2-trifluoro-ethyl)-1H-indole (269 mg, 1 mmol) in DMF (5 ml) at 0° C. The resulting mixture was stirred at 0° C. for half hour. 1-[4-(bromomethyl)phenyl]-1H-pyrrol (354 mg, 1.5 mmol) was then added to the reaction mixture at 0° C. The reaction temperature was raised to 25° C. and then the reaction mixture was stirred for 18 hours. NH4Cl (aq.) was added and extracted with EtOAc. The organic layer was washed with brine, then dried over anhydrous MgSO4. The solvent was distilled out under reduced pressure. Column chromatography (silica gel, EtOAc/hexanes (0% to 70%) yielded the title compound as a yellow solid.

Workup

  1. customat 0° C
  2. temperatureThe reaction temperature was raised to 25° C.
  3. stirringthe reaction mixture was stirred for 18 hours
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. distillationThe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-1631025a01754556bd2563d54c65948c
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07795446B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes