Water → HCID 67080515, compound

HRID 1048077Notes

Reaction equation

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

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of ethyl 7-(4-(3-bromo-4-fluorophenylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylate (54.8 mg, 0.0998 mmol), 4-chlorophenylboronic acid (20.299 mg, 0.129 mmol), Na2CO3 (31.75 mg, 0.299 mmol), tetrakis(triphenylphosphine)palladium(0) (5.769 mg, 0.0049 mmol), water (0.1 ml), and toluene (1 ml) in a vial was purged with Argon for few minutes and heated for 17 hours at 125° C. The crude mixture was purified on silica gel (EtOAc in hexanes gradient) to provide 41.4 mg of the title compound as a foamy solid (71%).

Workup

customwas purged with Argon for few minutes
customThe crude mixture was purified on silica gel (EtOAc in hexanes gradient)

Sources & evidence

ORD record: ord-bb8b144a539247fb9dd606946c28333d
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569522B2

Reaction notes

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