Sodium Carbonate → Ethyl 6-chloro-7-(4-(6-(3,4-dichlorophenyl)pyridin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate

HRID 1626429Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2[CH:33]=[CH:32][C:14]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([CH:20]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:21][CH2:22][O:23]4)=[CH:18][C:17]=3[Cl:31])=[CH:13][CH:12]=2)=[O:10])[CH:5]=[CH:4][CH:3]=1.[Cl:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][C:40]=1[Cl:41].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:31][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:16]=1[O:15][C:14]1[CH:32]=[CH:33][C:11]([C:9](=[O:10])[NH:8][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([C:38]4[CH:37]=[CH:36][C:35]([Cl:34])=[C:40]([Cl:41])[CH:39]=4)[N:7]=3)=[CH:12][CH:13]=1)[O:23][CH2:22][CH2:21][CH:20]2[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of ethyl 7-(4-(6-bromopyridin-2-ylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylate (0.050 g, 0.094 mmol), 3,4-dichlorophenylboronic acid (0.023 g, 0.12 mmol), and sodium carbonate (0.030 g, 0.28 mmol) in toluene (1 ml) and water (0.1 ml) degassed with argon was added tetrakis(triphenylphosphine)palladium (0.0054 g, 0.0047 mmol), and the reaction was heated to 100° C. for 16 hours. The reaction was loaded directly onto silica gel and eluted with a linear gradient of 5-70% EtOAc/hexanes to yield the desired compound (0.051 g, 0.085 mmol, 91% yield).

Workup

washeluted with a linear gradient of 5-70% EtOAc/hexanes

Sources & evidence

ORD record: ord-8b49af5223d74a33aeb2429446f1b073
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785445B2

Reaction notes

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