2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 66716432, compound

HRID 2271934Notes

Reaction equation

HRID 2271934 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[NH:17][CH:18]1[CH2:23][CH2:22][C:21]([N:25]([CH2:29][CH:30]=[CH2:31])[CH2:26][CH:27]=[CH2:28])([CH3:24])[CH2:20][CH2:19]1.[Cl:32][C:33]1[CH:38]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH:36]=[C:35]([Cl:48])[C:34]=1[OH:49]>>[CH:14]1([C:12]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[NH:17][CH:18]2[CH2:23][CH2:22][C:21]([N:25]([CH2:26][CH:27]=[CH2:28])[CH2:29][CH:30]=[CH2:31])([CH3:24])[CH2:20][CH2:19]2)=[CH:3][C:2]([C:37]2[CH:38]=[C:33]([Cl:32])[C:34]([OH:49])=[C:35]([Cl:48])[CH:36]=2)=[CH:11][CH:10]=3)=[O:13])[CH2:15][CH2:16]1

Participants

3

Reactant 2

HCID 667151272,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 66715388HCID 66715388, compound

Product 1

HCID 66716432HCID 66716432, compoundYield 27%

Procedure

Following general procedure F, {6-Bromo-4-[4-(diallylamino)-4-methylcyclohexylamino]quinolin-3-yl}(cyclopropyl)methanone (96 mg, 0.198 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (86 mg, 0.297 mmol) to afford the desired product (23 mg, 27%) as a yellow solid: ESI MS m/z 564 [C32H35Cl2N3O2+H]+.

Sources & evidence

ORD record
ord-bb7e5437a82c4333ad69b04ac8ba1a61
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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