Sodium Carbonate → HCID 178483664, compound

HRID 2271678Notes

Reaction equation

C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][C:12]([C:18]([CH:20]1[CH2:22][CH2:21]1)=[O:19])=[C:11]2[NH:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([CH2:30][N:31]([CH3:33])[CH3:32])[CH2:26][CH2:25]1.[Cl:34][C:35]1[CH:40]=[C:39](B2OC(C)(C)C(C)(C)O2)[CH:38]=[C:37]([Cl:50])[C:36]=1[OH:51]>>[CH:20]1([C:18]([C:12]2[CH:13]=[N:14][C:15]3[C:10]([C:11]=2[NH:23][C@H:24]2[CH2:25][CH2:26][C@H:27]([CH2:30][N:31]([CH3:33])[CH3:32])[CH2:28][CH2:29]2)=[CH:9][C:8]([C:39]2[CH:40]=[C:35]([Cl:34])[C:36]([OH:51])=[C:37]([Cl:50])[CH:38]=2)=[CH:17][CH:16]=3)=[O:19])[CH2:21][CH2:22]1

Participants

Reactant 3

HCID 10340Sodium Carbonate

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

HCID 178483663HCID 178483663, compound

Product 1

HCID 178483664HCID 178483664, compoundYield 59%

Procedure

Following general procedure F except 2M Na2CO3 was used instead of 1M Cs2CO3, (6-bromo-4-(trans-4-((dimethylamino)methyl)cyclohexylamino)quinolin-3-yl)(cyclopropyl)methanone (4.29 g, 9.96 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (4.32 g, 14.95 mmol) to afford the desired product (3.0 g, 59%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 9.77 (br s, 1H), 9.05 (s, 1H), 8.36 (d, J=2.1 Hz, 1H), 8.03 (dd, J=8.7, 1.8 Hz, 1H), 7.85 (d, J=8.7 Hz, 1H), 7.73 (s, 2H), 3.96-3.86 (m, 1H), 2.97-2.82 (m, 1H), 2.19 (s, 6H), 2.17-2.06 (m, 4H), 1.86 (d, J=12.7 Hz, 2H), 1.60-1.36 (m, 3H), 1.15-0.91 (m, 6H); APCI MS m/z 512 [C28H31Cl2N3O2+H]+; HPLC>99% (AUC), tR=5.15 min.

Sources & evidence

ORD record: ord-d39b9606f06947a29f7c475005ba082f
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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