4-(n-Boc-aminomethyl)-3-fluorobenzeneboronic acid pinacol ester → HCID 86696584, compound

HRID 1478308Notes

Reaction equation

HRID 1478308 reaction equation
Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([C:11]=1[CH3:12])=[C:9]([CH:13]1[CH2:15][CH2:14]1)[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]2=[O:20].[F:21][C:22]1[CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:25]=[CH:24][C:23]=1[CH2:37][NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42]>>[C:41]([O:40][C:39]([NH:38][CH2:37][C:23]1[CH:24]=[CH:25][C:26]([C:2]2[CH:3]=[CH:4][N:5]3[C:10]([C:11]=2[CH3:12])=[C:9]([CH:13]2[CH2:15][CH2:14]2)[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]3=[O:20])=[CH:27][C:22]=1[F:21])=[O:45])([CH3:44])([CH3:42])[CH3:43]

Participants

3

Reactant 2

HCID 669802924-(n-Boc-aminomethyl)-3-fluorobenzeneboronic acid pinacol esterHCID 86696543Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate

Product 1

HCID 86696584HCID 86696584, compoundYield 31.7%

Procedure

The general Suzuki coupling method described above was used to couple methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate with tert-butyl N-[[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]carbamate. Purification by flash silica column chromatography yielded methyl 8-[4-[(tert-butoxycarbonylamino)methyl]-3-fluoro-phenyl]-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate (24 mg, 31.7%).

Workup

  1. customPurification by flash silica column chromatography

Sources & evidence

ORD record
ord-8dc020d1fbb040faaef6b77506bb0f77
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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