N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide → HCID 44250487, compound

HRID 1619154Notes

Reaction equation

HRID 1619154 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH2:16][CH2:15][CH:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH2:13][CH2:12]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH:26]1([NH:29][C:30](=[O:47])[C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[C:33](B3OC(C)(C)C(C)(C)O3)[CH:32]=2)[CH2:28][CH2:27]1>>[CH:26]1([NH:29][C:30](=[O:47])[C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[C:33]([C:2]3[CH:10]=[C:9]4[C:5]([C:6]5([CH2:12][CH2:13][CH:14]([O:17][CH2:18][CH2:19][N:20]6[CH2:21][CH2:22][O:23][CH2:24][CH2:25]6)[CH2:15][CH2:16]5)[C:7](=[O:11])[NH:8]4)=[CH:4][CH:3]=3)[CH:32]=2)[CH2:27][CH2:28]1

Participants

3

Reactant 2

HCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 58154265HCID 58154265, compound

Product 1

HCID 44250487HCID 44250487, compound

Procedure

Obtained as a white solid (81%) as a single isomer (exact isomeric form not determined) from 6′-bromo-4-(2-morpholinoethoxy)spiro[cyclohexane-1,3′-indolin]-2′-one (preparation 27) and N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (preparation 40) following the experimental procedure as described in preparation 38 followed by purification by flash chromatography (98:2 to 20:1 dichloromethane/methanol).

Workup

  1. customas described in preparation 38
  2. customfollowed by purification by flash chromatography (98:2 to 20:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-1d97e9a8e6a4499eb62569258c0e83a0
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

Loading…