5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazol-3-amine → HCID 86696780, compound

HRID 1478383Notes

Reaction equation

HRID 1478383 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].CC1(C)C(C)(C)OB([C:29]2[CH:30]=[C:31]3[C:35](=[CH:36][CH:37]=2)[NH:34][N:33]=[C:32]3[NH2:38])O1>>[NH2:38][C:32]1[C:31]2[C:35](=[CH:36][CH:37]=[C:29]([C:2]3[CH:3]=[CH:4][N:5]4[C:10]([C:11]=3[CH3:12])=[C:9]([CH:13]3[CH2:15][CH2:14]3)[CH:8]=[C:7]([C:16]([O:18][CH3:19])=[O:17])[C:6]4=[O:20])[CH:30]=2)[NH:34][N:33]=1

Participants

3

Reactant 2

HCID 573569195-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazol-3-amineHCID 86696543Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylate

Product 1

HCID 86696780HCID 86696780, compoundYield 42%

Procedure

Methyl 8-(3-amino-1H-indazol-5-yl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared according to General Procedure A from methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (100 mg, 0.34 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazol-3-amine (106.4 mg, 0.41 mmol). Purification by flash silica column chromatography (DCM:MeOH) (1:0 to 9:1) afforded the title compound as a yellow solid (32 mg, 42%).

Workup

  1. customMethyl 8-(3-amino-1H-indazol-5-yl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was prepared
  2. customPurification by flash silica column chromatography (DCM:MeOH) (1:0 to 9:1)

Sources & evidence

ORD record
ord-8a7250c40b9c4931b1981fdf41f7cc7a
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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