Methyl Acrylate → HCID 118184948, compound

HRID 2177411Notes

Reaction equation

Br[C:2]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[N:14][S:15][C:16]=2[C:17]([F:20])([F:19])[F:18])=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[C:34]([O:38][CH3:39])(=[O:37])[CH:35]=[CH2:36]>CN(C=O)C>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:13]2[C:12]([CH2:11][O:10][C:7]3[CH:8]=[CH:9][C:2](/[CH:36]=[CH:35]/[C:34]([O:38][CH3:39])=[O:37])=[C:3]([CH:4]=[O:5])[CH:6]=3)=[C:16]([C:17]([F:20])([F:19])[F:18])[S:15][N:14]=2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 105 °C

Procedure

2-Bromo-5-((3-(4-chlorophenyl)-5-(trifluoromethyl)isothiazol-4-yl)methoxy)benzaldehyde (300 mg, 0.63 mmol), dichlorobis(tri-o-tolyphosphine) palladium (35 mg, 0.045 mmol), potassium carbonate (174 mg, 1.26 mmol) in DMF (2 mL) was purged under reduced pressure and backfilled with argon gas. Methyl acrylate (0.114 mL, 1.26 mmol) was added and heated at 105° C. for 3 hrs. The reaction mixture was filtered through a pad of diatomaceous earth. The filtrate was washed with ethyl acetate. The organic layers were washed with water and brine, dried, filtered, and the filtrate was then concentrated. The resultant residue was purified by column chromatography on a 50 g silica gel column, eluting with 0-20% ethyl acetate/heptanes, to give compound 267b as a yellow solid (125 mg, 41% yield).

Workup

filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
washThe filtrate was washed with ethyl acetate
washThe organic layers were washed with water and brine
customdried
filtrationfiltered
concentrationthe filtrate was then concentrated
customThe resultant residue was purified by column chromatography on a 50 g silica gel column
washeluting with 0-20% ethyl acetate/heptanes

Sources & evidence

ORD record: ord-18633c1272b244cc8204d3d4ea6a996a
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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