2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 66716612, compound

HRID 2271870Notes

Reaction equation

HRID 2271870 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][N:21]([CH:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)[CH:22]=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][N:21]([CH:23]4[CH2:24][CH2:25][N:26]([CH3:29])[CH2:27][CH2:28]4)[CH:22]=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])[CH2:15][CH2:16]1

Participants

3

Reactant 2

HCID 667151272,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 66716300HCID 66716300, compound

Product 1

HCID 66716612HCID 66716612, compoundYield 63%

Procedure

Following general procedure D, (6-bromo-4-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-ylamino) quinoline-3-yl)(cyclopropyl)methanone (50 mg, 0.11 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (49 mg, 0.17 mmol) to afford the desired product (36 mg, 63%) as a yellow solid: 1H NMR (500 MHz, CD3OD+TFA-d) δ 9.45 (s, 1H), 8.23 (d, J=9.0 Hz, 1H), 8.01 (d, J=9.2 Hz, 2H), 7.68 (s, 1H), 7.40 (s, 1H), 4.62 (m, 1H), 3.68 (d, J=12.8 Hz, 2H), 3.41 (m, 1H), 3.25 (m, 2H), 2.94 (s, 3H), 2.37 (m, 3H), 1.22 (m, 3H); ESI MS m/z 536 [C28H27Cl2N5O2+H]+; HPLC 98.4% (AUC), tR=10.57 min.

Sources & evidence

ORD record
ord-0a1cae38902645f79bd7d4976d133f88
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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