2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 66716220, compound

HRID 2271735Notes

Reaction equation

HRID 2271735 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][N:21]([CH3:24])[CH2:20][CH2:19]1.[CH3:25][O:26][C:27]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[CH:29][C:28]=1[OH:42]>>[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[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]2)=[CH:3][C:2]([C:31]2[CH:30]=[CH:29][C:28]([OH:42])=[C:27]([O:26][CH3:25])[CH:32]=2)=[CH:11][CH:10]=3)=[O:13])[CH2:15][CH2:16]1

Participants

3

Reactant 2

HCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 66716363HCID 66716363, compound

Product 1

HCID 66716220HCID 66716220, compoundYield 63.2%

Procedure

Following general procedure F, [6-bromo-4-(1-methylpiperidin-4-ylamino)quinolin-3-yl](cyclopropyl)methanone (47 mg, 0.121 mmol) was reacted with 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (45 mg, 0.182 mmol) to afford the desired product (33 mg, 63%) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ 9.17 (s, 1H), 8.33 (d, J=1.8 Hz, 1H), 8.05 (dd, J=8.7, 1.9 Hz, 1H), 7.92 (d, J=8.7 Hz, 1H), 7.27 (d, J=2.1 Hz, 1H), 7.19 (dd, J=8.2, 2.1 Hz, 1H), 6.94 (d, J=8.2 Hz, 1H), 4.36 (s, 1H), 3.97 (s, 3H), 3.34 (s, 1H), 3.08 (s, 2H), 2.94-2.82 (m, 1H), 2.65 (s, 2H), 2.53 (s, 3H), 2.28 (d, J=13.9 Hz, 2H), 1.89 (d, J=10.3 Hz, 2H), 1.26-1.17 (m, 2H), 1.17-1.08 (m, 2H); ESI MS m/z 432 [C26H29N3O3+H]+; HPLC (AUC), tR=9.78 min.

Sources & evidence

ORD record
ord-87c055d3904643ca8e4a38d6fd751535
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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