2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 178487418, compound

HRID 2271699Notes

Reaction equation

HRID 2271699 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][C@@H:18]1[CH2:23][CH2:22][C@H:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][CH2:19]1.[CH3:32][O:33][C:34]1[CH:39]=[C:38](B2OC(C)(C)C(C)(C)O2)[CH:37]=[CH:36][C:35]=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][C@@H:18]2[CH2:23][CH2:22][C@H:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:30])[CH3:28])[CH2:20][CH2:19]2)=[CH:3][C:2]([C:38]2[CH:37]=[CH:36][C:35]([OH:49])=[C:34]([O:33][CH3:32])[CH:39]=2)=[CH:11][CH:10]=3)=[O:13])[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 178454008HCID 178454008, compound

Product 1

HCID 178487418HCID 178487418, compoundYield 98.6%

Procedure

Following general procedure F, tert-butyl cis-4-[6-bromo-3-(cyclopropanecarbonyl)quinolin-4-ylamino]cyclohexylcarbamate (40 mg, 0.082 mmol) was reacted with 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (31 mg, 0.124 mmol) to afford the crude product (43 mg) as a yellow solid: ESI MS m/z 532 [C31H37N3O5+H]+.

Sources & evidence

ORD record
ord-c2bba1f6d7be4f0399b1a71f5514c3ce
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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