2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 66715584, compound

HRID 2271962Notes

Reaction equation

HRID 2271962 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:18]1[CH:23]=[CH:22][C:21]([CH:24]([OH:29])[CH2:25][N:26]([CH3:28])[CH3:27])=[CH:20][CH:19]=1.[Cl:30][C:31]1[CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:34]=[C:33]([Cl:46])[C:32]=1[OH:47]>>[CH:14]1([C:12]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[NH:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]([OH:29])[CH2:25][N:26]([CH3:27])[CH3:28])=[CH:20][CH:19]=2)=[CH:3][C:2]([C:35]2[CH:36]=[C:31]([Cl:30])[C:32]([OH:47])=[C:33]([Cl:46])[CH:34]=2)=[CH:11][CH:10]=3)=[O:13])[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 667151272,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 86692894HCID 86692894, compound

Product 1

HCID 66715584HCID 66715584, compoundYield 69.5%

Procedure

Following general procedure F, {6-bromo-4-[4-(2-(dimethylamino)-1-hydroxyethyl)phenylamino]quinolin-3-yl}(cyclopropyl)methanone (50 mg, 0.110 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (48 mg, 0.165 mmol) to afford the desired product (41 mg, 69%) as a yellow solid: 1H NMR (300 MHz, CD3OD+TFA-d) δ 9.38 (s, 1H), 8.22 (dd, J=8.8, 2.0 Hz, 1H), 8.07-7.98 (m, 2H), 7.65 (d, J=8.4 Hz, 2H), 7.48 (d, J=8.4 Hz, 2H), 7.38 (s, 2H), 5.18 (dd, J=9.8, 4.3 Hz, 1H), 3.25-3.14 (m, 2H), 3.02 (s, 3H), 2.95 (s, 3H), 2.86-2.79 (m, 1H), 1.22-1.11 (m, 4H); ESI MS m/z 536 [C29H27Cl2N3O3+H]+; HPLC 95.1% (AUC), tR=11.42 min.

Sources & evidence

ORD record
ord-226abdd0c35d4b60932ecfd28958e9d2
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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