HCID 118324033, compound → HCID 118324119, compound

HRID 1778311Notes

Reaction equation

HRID 1778311 reaction equation
[C:1]([O:5][C:6]1[CH:15]=[C:14](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:25]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=[O:26])[CH:12]=2)[N:7]=1)([CH3:4])([CH3:3])[CH3:2].[S:34]1[CH:38]=[CH:37][C:36]([Mg]Br)=[CH:35]1>C1COCC1>[C:1]([O:5][C:6]1[CH:15]=[C:14](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:25]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)([C:36]3[CH:37]=[CH:38][S:34][CH:35]=3)[OH:26])[CH:12]=2)[N:7]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 118324033HCID 118324033, compoundHCID 178419642HCID 178419642, compound

Product 1

HCID 118324119HCID 118324119, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-(2-(tert-butoxy)-4-(3-fluorostyryl)quinolin-6-yl)(4-chlorophenyl)methanone (90 mg, 0.196 mmol) in THF (2 mL) was slowly added thiophen-3-ylmagnesium bromide (1.04 mL, 0.313 mmol, 0.3M in toluene) and the resulting solution was kept at 0° C. for 3 hr. The reaction was quenched with saturated NH4Cl at 0° C. and the aqueous layer was extracted with EtOAc. The combined organics were purified by silica column chromatography (20-30% EtOAc/hexanes) to yield (E)-(2-(tert-butoxy)-4-(3-fluorostyryl)quinolin-6-yl)(4-chlorophenyl)(thiophen-3-yl)methanol.

Workup

  1. customThe reaction was quenched with saturated NH4Cl at 0° C.
  2. extractionthe aqueous layer was extracted with EtOAc
  3. customThe combined organics were purified by silica column chromatography (20-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-232208a7f6cc40f995e06523779faf2a
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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