Water → HCID 57887232, compound

HRID 1819511Notes

Reaction equation

HRID 1819511 reaction equation
[F:1][C:2]1[C:7]([CH:8]([O:14][CH3:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:6][CH:5]=[CH:4][C:3]=1[C:16]1[N:17]=[C:18]([NH2:21])[S:19][CH:20]=1.Br[C:23]1[CH:28]=[C:27]([F:29])[C:26](/[CH:30]=[C:31](\[O:36][CH3:37])/[C:32]([O:34][CH3:35])=[O:33])=[C:25]([F:38])[CH:24]=1.C(N(CC)CC)C.O.CN([CH:50]=[O:51])C>>[F:29][C:27]1[CH:28]=[C:23]([C:50](=[O:51])[NH:21][C:18]2[S:19][CH:20]=[C:16]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([CH:8]([O:14][CH3:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:2]=3[F:1])[N:17]=2)[CH:24]=[C:25]([F:38])[C:26]=1/[CH:30]=[C:31](\[O:36][CH3:37])/[C:32]([O:34][CH3:35])=[O:33]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 23119177HCID 23119177, compoundHCID 57887225HCID 57887225, compound

Product 1

HCID 57887232HCID 57887232, compound

Conditions

Temperature
85 °C

Procedure

4-[2-Fluoro-3-(1-methyloxyhexyl)phenyl]thiazol-2-ylamine (460 mg) and methyl (Z)-3-(4-bromo-2,6-difluorophenyl)-2-methyloxyacrylate (462 mg), and dichlorobistriphenylphosphinepalladium (150 mg) were dissolved in DMF (6 mL). Triethylamine (0.84 mL) was added into the mixture, and the reaction mixture was stirred under carbon monoxide atomosphere at 85° C. for 16 h. Water added into the reaction mixture, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, and brine, dried over magnesium sulfate, evaporated. The obtained residue was purified by Colum chromatography (hexane:ethyl acetate=4:1) to obtain the compound (24) 630 mg.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water, and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe obtained residue was purified by Colum chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-2b0f42a615234deeb86f233878902e76
Source dataset
uspto-grants-2009_10
Patent number
US07601746B2

Reaction notes

Loading…