2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 178450276, compound

HRID 2271949Notes

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](=[O:16])[CH2:13][CH2:14][CH3:15])=[C:5]2[NH:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([CH2:24][N:25]([CH3:27])[CH3:26])[CH2:20][CH2:19]1.[Cl:28][C:29]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[C:31]([Cl:44])[C:30]=1[OH:45]>>[Cl:28][C:29]1[CH:34]=[C:33]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12](=[O:16])[CH2:13][CH2:14][CH3:15])=[C:5]3[NH:17][C@H:18]2[CH2:19][CH2:20][C@H:21]([CH2:24][N:25]([CH3:27])[CH3:26])[CH2:22][CH2:23]2)[CH:32]=[C:31]([Cl:44])[C:30]=1[OH:45]

Participants

Reactant 2

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

HCID 178450269HCID 178450269, compound

Product 1

HCID 178450276HCID 178450276, compoundYield 35.3%

Procedure

Following general procedure A-1, 1-{6-bromo-4-[trans-4-((dimethylamino)methyl)cyclohexylamino]quinolin-3-yl}butan-1-one (48 mg, 0.110 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (47 mg, 0.165 mmol) to afford the desired product (20 mg, 35%) as a yellow solid: 1H NMR (500 MHz, CD3OD+TFA-d) δ 9.14 (s, 1H), 8.47 (s, 1H), 8.27 (dd, J=8.7, 1.8 Hz, 1H), 8.98 (d, J=8.7 Hz, 1H), 7.72 (s, 2H), 4.53 (s, 1H), 3.16-3.06 (m, 4H), 2.94 (s, 6H), 2.50-2.43 (m, 2H), 2.08-2.02 (m, 3H), 1.88-1.74 (m, 4H), 1.39-1.32 (m, 1H), 1.06 (t, J=7.4 Hz, 3H); ESI MS m/z 514 [C28H33Cl2N3O2+H]+; HPLC 98.7% (AUC), tR=11.27 min.

Sources & evidence

ORD record: ord-727b78564dc44fecbebf7aede1b87d4b
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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