Allyl bromide → HCID 89611162, compound

HRID 869070Notes

Reaction equation

HRID 869070 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[C:15]3[C:11](=[N:12][N:13]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])[C:14]=3[CH:24]([CH3:26])[CH3:25])[C:10]2=[O:35])[CH:5]=[CH:6][C:7]=1[F:8].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:46](Br)[CH:47]=[CH2:48]>>[CH2:48]([C:16]1([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[C:15]2[C:11](=[N:12][N:13]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])[C:14]=2[CH:24]([CH3:26])[CH3:25])[C:10](=[O:35])[N:9]1[C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1)[CH:47]=[CH2:46]

Participants

4

Reactant 3

HCID 7841Allyl bromideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 89601326HCID 89601326, compound

Product 1

HCID 89611162HCID 89611162, compound

Procedure

The title compound was prepared in analogy to the procedure described for example 74 but using the compound prepared in example 88, 2 equivalents of KHMDS and 2 equivalents of allyl bromide. The reaction mixture was stirred for 1 h at rt and quenched by addition of a saturated solution of ammonium chloride. The crude material was purified by silica gel column chromatography (hexane/EtOAc, 4:1). tR: 6.90 min (HPLC 2); ESI-MS: 550.1 [M+H]+ (LC-MS 2); Rf=0.55 (hexane/EtOAc, 1:1).

Workup

  1. customquenched by addition of a saturated solution of ammonium chloride
  2. customThe crude material was purified by silica gel column chromatography (hexane/EtOAc, 4:1)

Sources & evidence

ORD record
ord-5940c454ba2d4ea3a0d00b0ae5921c9c
Source dataset
uspto-grants-2015_03
Patent number
US08969341B2

Reaction notes

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