2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 66715650, compound

HRID 2271909Notes

Reaction equation

HRID 2271909 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]=[CH:20][C:21]([O:24][CH2:25][CH2:26][NH:27]C(=O)OC(C)(C)C)=[N:22][CH:23]=1.[Cl:35][C:36]1[CH:41]=[C:40](B2OC(C)(C)C(C)(C)O2)[CH:39]=[C:38]([Cl:51])[C:37]=1[OH:52]>>[NH2:27][CH2:26][CH2:25][O:24][C:21]1[N:22]=[CH:23][C:18]([NH:17][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([C:40]4[CH:41]=[C:36]([Cl:35])[C:37]([OH:52])=[C:38]([Cl:51])[CH:39]=4)[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:12]([CH:14]2[CH2:15][CH2:16]2)=[O:13])=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 667151272,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 66715668HCID 66715668, compound

Product 1

HCID 66715650HCID 66715650, compoundYield 22%

Procedure

Following general procedure D, tert-butyl 2-(5-(6-bromo-3-(cyclopropanecarbonyl)quinolin-4-ylamino)pyridin-2-yloxy)ethylcarbamate (100 mg, 0.19 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (81 mg, 0.28 mmol) to obtain the protected intermediate which was subjected to general procedure A-2 to afford the desired product (21 mg, 22% over two steps) as a yellow solid: 1H NMR (500 MHz, CD3OD+TFA-d) δ 9.40 (s, 1H), 8.33-8.24 (m, 2H), 8.13-8.04 (m, 2H), 7.83 (dd, J=8.8, 2.8 Hz, 1H), 7.37 (s, 2H), 7.14 (d, J=8.8 Hz, 1H), 4.66 (t, J=5.1 Hz, 2H), 3.43 (t, J=5.1 Hz, 2H), 2.87-2.80 (m, 1H), 1.22-1.15 (m, 4H); ESI MS m/z 509 [C26H22Cl2N4O3+H]+; HPLC 99.7% (AUC), tR=11.26 min.

Workup

  1. customto obtain the protected intermediate which

Sources & evidence

ORD record
ord-c1978798111244da95f817b875ec974b
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

Loading…