2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 66715555, compound

HRID 2271955Notes

Reaction equation

HRID 2271955 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:19]=[N:20][C:21]([CH2:24][N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:22][CH:23]=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:19]=[N:20][C:21]([CH2:24][N:25]4[CH2:26][CH2:27][CH2:28][CH2:29]4)=[CH:22][CH:23]=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 66715896{6-Bromo-4-[6-(pyrrolidin-1-ylmethyl)pyridin-3-ylamino]quinolin-3-yl}(cyclopropyl)methanone

Product 1

HCID 66715555HCID 66715555, compoundYield 64%

Procedure

Following general procedure F, {6-Bromo-4-[6-(pyrrolidin-1-ylmethyl)pyridin-3-ylamino]quinolin-3-yl}(cyclopropyl)methanone (45 mg, 0.100 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (43 mg, 0.150 mmol) to afford the desired product (34 mg, 64%) as a yellow solid: 1H NMR (500 MHz, CD3OD+TFA-d) δ 9.40 (s, 1H), 8.72 (d, J=2.5 Hz, 1H), 8.30 (dd, J=8.8, 2.0 Hz, 1H), 8.16-8.06 (m, 2H), 7.96 (dd, J=8.3, 2.5 Hz, 1H), 7.65 (d, J=8.3 Hz, 1H), 7.46 (s, 2H), 4.65 (s, 2H), 3.63-3.59 (m, 2H), 3.21-3.12 (m, 2H), 2.85-2.76 (m, 1H), 2.20-2.16 (m, 2H), 2.09-2.01 (m, 2H), 1.20-1.10 (m, 4H); ESI MS m/z 533 [C29H26Cl2N4O2+H]+; HPLC 98.8% (AUC), tR=10.76 min.

Sources & evidence

ORD record
ord-859a0623a50b4bbbb30f00d82add081b
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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