2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 66715476, compound

HRID 2271755Notes

Reaction equation

HRID 2271755 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]([CH2:24][N:25]([CH3:27])[CH3:26])=[CH:20][CH: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]>>[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]([CH2:24][N:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=2)=[CH:3][C:2]([C:33]2[CH:34]=[C:29]([Cl:28])[C:30]([OH:45])=[C:31]([Cl:44])[CH:32]=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 66715207HCID 66715207, compound

Product 1

HCID 66715476HCID 66715476, compoundYield 73%

Procedure

Following general procedure F, (6-bromo-4-{4-[(dimethylamino)methyl]phenylamino}quinolin-3-yl)(cyclopropyl)methanone (44 mg, 0.104 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (45 mg, 0.156 mmol) to afford the desired product (38 mg, 73%) as a yellow solid: 1H NMR (300 MHz, CD3OD+Acetic Acid-d4) δ 9.26 (s, 1H), 7.99 (d, J=10.0 Hz, 2H), 7.94 (s, 1H), 7.51 (d, J=8.4 Hz, 2H), 7.29 (s, J=9.9 Hz, 3H), 7.25 (s, 1H), 4.32 (s, 2H), 2.94-2.85 (m, 1H), 2.82 (s, 6H), 1.17-1.01 (m, 4H); ESI MS m/z 506 [C28H25Cl2N3O2+H]+; HPLC 94.4% (AUC), tR=11.19 min.

Sources & evidence

ORD record
ord-44b1b58fc9fa4fe5ac8ef85df449eb91
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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