N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide → Isopropyl 4-{5-[6-(methylcarbamoyl)pyridin-3-yl]benzo[d]oxazol-2-yl}piperidine-1-carboxylate

HRID 710166

Reaction equation

HRID 710166 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)=[N:7][C:6]=2[CH:22]=1.[CH3:23][NH:24][C:25](=[O:41])[C:26]1[CH:31]=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][N:27]=1>>[CH3:23][NH:24][C:25]([C:26]1[N:27]=[CH:28][C:29]([C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8]([CH:10]4[CH2:15][CH2:14][N:13]([C:16]([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]4)=[N:7][C:6]=3[CH:22]=2)=[CH:30][CH:31]=1)=[O:41]

Participants

3

Reactant 2

HCID 44119560N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamideHCID 71257568Isopropyl 4-(5-bromobenzo[d]oxazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 71257260Isopropyl 4-{5-[6-(methylcarbamoyl)pyridin-3-yl]benzo[d]oxazol-2-yl}piperidine-1-carboxylateYield 5.8%

Procedure

Following the General Procedure-1, the titled compound (20 mg) was prepared from Intermediate 13 (300 mg, 0.82 mmol) and N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide (256 mg, 0.98 mmol) as a brown solid. M.P.: 158-161° C. MS (m/z): 423.5 [M+H]+.

Sources & evidence

ORD record
ord-ac475505ca714dffa884cb922dd6c260
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Linked notes

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