Sodium Carbonate → HCID 67288556, compound

HRID 1626437Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:28])[NH:20][C:21]3[N:22]=[N:23][C:24](Cl)=[CH:25][CH:26]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:29]([O:31][CH2:32][CH3:33])=[O:30].[Cl:34][C:35]1[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[CH:37][C:36]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19](=[O:28])[NH:20][C:21]3[N:22]=[N:23][C:24]([C:36]4[CH:37]=[CH:38][C:39]([C:41]([F:44])([F:43])[F:42])=[CH:40][C:35]=4[Cl:34])=[CH:25][CH:26]=3)=[CH:17][CH:18]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of ethyl 6-chloro-7-(4-(6-chloropyridazin-3-ylcarbamoyl)phenoxy)chroman-4-carboxylate (0.131 g, 0.268 mmol), 2-chloro-4-(trifluoromethyl)phenylboronic acid (0.0903 g, 0.402 mmol), and 20% aqueous sodium carbonate (0.426 ml, 0.805 mmol) in toluene (2 ml) was degassed with argon, then tetrakis(triphenylphosphine)palladium (0.0155 g, 0.0134 mmol) was added and the reaction was heated to 110° C. for 16 hours. The reaction mixture was loaded directly onto silica gel and purified eluting with a linear gradient of 5-70% EtOAc/hexanes to yield the desired compound (0.034 g, 0.0538 mmol, 20.0% yield).

Workup

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

Sources & evidence

ORD record: ord-fc2ee7be85734464aa0d8a19c433a91e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785445B2

Reaction notes

Loading…