Benzyl Bromide → HCID 178515726, compound

HRID 1741667Notes

Reaction equation

HRID 1741667 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:6][N:7]1[C:11](=[O:12])[C:10](=[CH:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[NH:9][C:8]1=[O:23].C([Li])CCC.[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:38]([N:9]1[C:10](=[CH:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[C:11](=[O:12])[N:7]([CH2:6][C:5]2[CH:4]=[C:3]([C:2]([F:1])([F:31])[F:32])[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=2)[C:8]1=[O:23])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 25517Ammonium ChlorideHCID 178418339ButyllithiumHCID 178517688HCID 178517688, compound

Product 1

HCID 178515726HCID 178515726, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound of Example 2 (0.5 g) in dry tetrahydrofuran (20 ml) was cooled to -78° C. and n-butyl lithium (0.72 ml of a 1.6M solution in hexanes) was added with stirring. After 15 minutes benzyl bromide (0.14 ml) was added. The solution was allowed to warm to room temperature then heated to reflux for 3 hours, cooled and poured into saturated ammonium chloride solution (20 ml). This mixture was extracted with ethyl acetate and the organic layers dried (MgSO4). The residue was purified by chromatography on silica gel eluting with ethyl acetate-petroleum ether (1:3) to give the title compound, mp 154°-156° C.; found: C, 61.66; H, 4.05; N, 7.64; C28H21F6N3O2 requires: C, 61.65; H, 3.88; N, 7.70.

Workup

  1. temperaturethen heated
  2. temperatureto reflux for 3 hours
  3. temperaturecooled
  4. extractionThis mixture was extracted with ethyl acetate
  5. dry with materialthe organic layers dried (MgSO4)
  6. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate-petroleum ether (1:3)

Sources & evidence

ORD record
ord-2bbf37d215a94ede949135ba0f44c5d5
Source dataset
uspto-grants-1994_08
Patent number
US05334606

Reaction notes

Loading…