Sodium hydride → HCID 21865550, compound

HRID 857290Notes

Reaction equation

HRID 857290 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C:13]2[CH:14]=[C:15]([C:19]3[CH:20]=[C:21]([C:29]([CH3:33])([CH3:32])[C:30]#[N:31])[CH:22]=[C:23]4[C:28]=3[N:27]=[CH:26][CH:25]=[CH:24]4)[CH:16]=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)(=O)=O.[H-].[Na+].[F:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41]Br)=[CH:39][CH:38]=1>CN(C=O)C.[NH4+].[Cl-]>[F:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41][N:11]([CH2:12][C:13]2[CH:14]=[C:15]([C:19]3[CH:20]=[C:21]([C:29]([CH3:33])([CH3:32])[C:30]#[N:31])[CH:22]=[C:23]4[C:28]=3[N:27]=[CH:26][CH:25]=[CH:24]4)[CH:16]=[CH:17][CH:18]=2)[C:8]2[CH:9]=[CH:10][C:5]([S:2][CH3:1])=[CH:6][CH:7]=2)=[CH:39][CH:38]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 21865597HCID 21865597, compound

Product 1

HCID 21865550HCID 21865550, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To solution of 2-(8-{3-[(4-Methanesulfonyl-phenylamino)-methyl]-phenyl}-quinolin-6-yl)-2-methyl-propionitrile from EXAMPLE 36 (Step 1) (1.0 eq) in DMF (0.2M) was added NaH (60% dispersion in oil; 4.0 eq). The resulting mixture was stirred for 10 min then 4-fluorobenzyl bromide (3.0 eq) was added. The mixture was stirred for 12 h, poured in saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 4:1) afforded the desired compound as a foam.

Workup

  1. stirringThe mixture was stirred for 12 h
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1cb6e72c592c416581a30752fa9831ce
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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