tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazole-1-carboxylate → HCID 178497212, compound

HRID 1478373Notes

Reaction equation

HRID 1478373 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:44]=[CH:43][C:32]3[N:33](C(OC(C)(C)C)=O)[CH:34]=[N:35][C:31]=3[CH:30]=2)O1.CC1(C)C(C)(C)OB(C2C=CC3N=CN(C(OC(C)(C)C)=O)C=3C=2)O1>>[NH:33]1[C:32]2[CH:43]=[CH:44][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][C:31]=2[N:35]=[CH:34]1

Participants

4

Reactant 3

HCID 59477219tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazole-1-carboxylateHCID 86696543Methyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-quinolizine-3-carboxylateHCID 86696770HCID 86696770, compound

Product 1

HCID 178497212HCID 178497212, compound

Procedure

Methyl 8-(1H-benzo[d]imidazol-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 (75 mg, 0.26 mmol) and a mixture of tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole-1-carboxylate and tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole-1-carboxylate (141.5 mg, 0.41 mmol). Purification by flash silica column chromatography (DCM:MeOH) (1:0 to 9:1) afforded the title BOC-deprotected compound as a yellow solid (69.9 mg, 65%).

Workup

  1. customPurification by flash silica column chromatography (DCM:MeOH) (1:0 to 9:1)

Sources & evidence

ORD record
ord-134b35f6c5be46b68905474b6b012a31
Source dataset
uspto-grants-2016_08
Patent number
US09403818B2

Reaction notes

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