HCID 58065823, compound → HCID 71253947, compound

HRID 1028314Notes

Reaction equation

HRID 1028314 reaction equation
[CH3:1][Mg]Br.[Br:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH2:19][C:20](=[O:29])[CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([Br:18])=[CH:12][CH:11]=3>C1COCC1>[Br:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH2:19][C:20]([CH3:1])([OH:29])[CH2:21][O:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([Br:18])=[CH:12][CH:11]=3

Participants

4

Reactant 2

HCID 58065823HCID 58065823, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 71253947HCID 71253947, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (92 μl, 3.0 M in THF) was added to an ice-cooled solution of title compound of example 103, step 1, 1-(3,6-dibromo-9H-carbazol-9-yl)-3-phenoxypropan-2-one (86 mg, 0.18 mmol) in anhydrous THF (1.8 ml). The reaction was stirred in the gently warming ice bath for 6 hours, and then quenched by addition of water. The crude mixture was diluted with EtOAc and washed with saturated sodium bicarbonate, water and then brine. The organic layer was dried over Na2SO4, filtered and condensed. Some unreacted starting material was precipitated from ˜50% acetone/hexanes. The condensed filtrate was carried forward. Yield=89%. MS (ESI), m/z: calculated 486.98. found 531.7 (M+HCOO−).

Sources & evidence

ORD record
ord-021ddd86244c404186117e2ea045e6a4
Source dataset
uspto-grants-2014_05
Patent number
US08735440B2

Reaction notes

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