Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate → tert-Butyl (S)-4-(5-(1-(((benzyloxy)carbonyl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-3,6-dihydropyridine-1(2H)-carboxylate

HRID 2205613Notes

Reaction equation

HRID 2205613 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH:14]=2)O1.Br[C:24]1[CH:25]=[C:26]2[N:45]([CH3:46])[CH:44]=[CH:43][C:27]2=[N:28][C:29]=1[C@@H:30]([NH:32][C:33](=[O:42])[O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH3:31]>>[CH2:35]([O:34][C:33]([NH:32][C@H:30]([C:29]1[N:28]=[C:27]2[CH:43]=[CH:44][N:45]([CH3:46])[C:26]2=[CH:25][C:24]=1[C:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:13][CH:14]=1)[CH3:31])=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

3

Reactant 2

HCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 118214750Benzyl (S)-(1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate

Product 1

HCID 118214754tert-Butyl (S)-4-(5-(1-(((benzyloxy)carbonyl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-3,6-dihydropyridine-1(2H)-carboxylate

Procedure

The title compound was prepared similar to STEP A in PREPARATION 17 using tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate and benzyl (S)-(1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate as starting materials.

Sources & evidence

ORD record
ord-1cc7173cd610432d9baf7d608165c2c7
Source dataset
uspto-grants-2016_06
Patent number
US09371321B2

Reaction notes

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