Methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate → Methyl 4-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-5-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

HRID 529030Notes

Reaction equation

HRID 529030 reaction equation
Br[C:2]1[N:6]([CH3:7])[CH:5]=[N:4][C:3]=1[C:8]([N:10]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14])=[O:9].CC1(C)COB([C:26]2[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][C:27]=2[C:36]([N:38]2[CH2:47][CH2:46][C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH2:39]2)=[O:37])OC1>>[CH2:11]([N:10]([CH2:15][CH2:16][CH2:17][CH3:18])[C:8]([C:3]1[N:4]=[CH:5][N:6]([CH3:7])[C:2]=1[C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][C:27]=1[C:36]([N:38]1[CH2:47][CH2:46][C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39]1)=[O:37])=[O:9])[CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 71060775Methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate2×HCID 710624155-bromo-N,N-dibutyl-1-methyl-1H-imidazole-4-carboxamide

Product 1

HCID 71062493Methyl 4-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-5-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoateYield 40%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 264I, 5-bromo-N,N-dibutyl-1-methyl-1H-imidazole-4-carboxamide (600 mg, 1.9 mmol) and methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (Intermediate 264H, 1.55 g, 3.8 mmol) were converted to the title compound (400 mg, 40%). MS(ESI+) m/z 531.6 (M+H)+.

Sources & evidence

ORD record
ord-6d307d55a99d4e6ca190336d3b5146f0
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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