Sodium Carbonate → HCID 59300550, compound

HRID 2235932Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[C@H:18]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:17][CH2:16]3)[CH:5]=[CH:4][C:3]=1[C:28]([F:31])([F:30])[F:29].O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+].[CH3:44][O:45][C:46]1[CH:51]=[CH:50][C:49](B(O)O)=[CH:48][CH:47]=1>C1(C)C=CC=CC=1.O>[CH3:44][O:45][C:46]1[CH:51]=[CH:50][C:49]([C:2]2[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[C@H:18]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:17][CH2:16]4)[CH:5]=[CH:4][C:3]=2[C:28]([F:31])([F:30])[F:29])=[CH:48][CH:47]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl [(1S-5-(3-{[6-chloro-5-(trifluoromethyl)-2-pyridinyl]amino}propoxy)-2,3-dihydro-1H-inden-1-yl]acetate (Example 303, 0.06 9, 0.14 mmol) in a mixture of toluene (3.75 mL), 1,4-dioxane (0.75 mL), and water (0.88 mL) were added Na2CO3 (0.15 g, 1.38 mmol), 4-methoxyphenyl boronic acid (0.08 g, 0.55 mmol), and PdCl2(dppf)CH2Cl2 (0.02 g, 0.03 mmol). The mixture was heated at 80° C. for 4 h, and then concentrated under reduced pressure. The product (0.11 g, 94%) was purified by silica gel flash chromatography (2:1 hexanes /EtOAc). 1H NMR (400 MHz, DMSO-d6) δ 7.66 (d, 1H), 7.39 (t, 1H), 7.33 (d, 2H), 7.04 (d, 1H), 6.94 (dd, 2H), 6.74 (d, 1H), 6.65 (dd, 1H), 6.50 (d, 1H), 4.08 (q, 2H), 3.97 (t, 2H), 3.79 (s, 3H), 3.45-3.30 (m, 3H), 2.76-2.68 (m, 3H), 2.35 (dd, 1H), 2.30-2.20 (m, 1H), 1.95 (qt, 2H), 1.70-1.58 (m, 1H), 1.19 (t, 3H).

Workup

concentrationconcentrated under reduced pressure
customThe product (0.11 g, 94%) was purified by silica gel flash chromatography (2:1 hexanes /EtOAc)

Sources & evidence

ORD record: ord-4b83df436e7245c091a121a8c6da1839
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714004B2

Reaction notes

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