Sodium Carbonate → (Z)-N-(1-(4-(4-Isopropylphenyl)phenyl)-1-(3-thienyl)prop-1-en-3-yl)sarcosine

HRID 433277Notes

Reaction equation

HRID 433277 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)=[CH:9]/[CH2:10][N:11]([CH2:13][C:14]([OH:16])=[O:15])[CH3:12])=[CH:4][CH:3]=1.[CH:22]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)([CH3:24])[CH3:23].C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.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>[CH:22]([C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:7]=[CH:6][C:5](/[C:8](/[C:17]3[CH:21]=[CH:20][S:19][CH:18]=3)=[CH:9]/[CH2:10][N:11]([CH2:13][C:14]([OH:16])=[O:15])[CH3:12])=[CH:4][CH:3]=2)=[CH:27][CH:26]=1)([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27734804-Isopropylphenylboronic acidHCID 18758598(Z)-N-(1-(4-bromophenyl)-1-(3-thienyl)prop-1-en-3-yl)sarcosine

Product 1

HCID 10272664(Z)-N-(1-(4-(4-Isopropylphenyl)phenyl)-1-(3-thienyl)prop-1-en-3-yl)sarcosine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of (Z)-N-(1-(4-bromophenyl)-1-(3-thienyl)prop-1-en-3-yl)sarcosine, tbutyl ester E(i) (21.14 g, 50.05 mmol) in dimethoxyethane (210 mL) was added 4-isopropylbenzeneboronic acid (16.41 g, 100.1 mmol), Pd(PPh3)4 (2.89 g, 2.50 mmol), and 2M Na2CO3 (210 mL). The vigorously stirred mixture was heated to reflux for 2 hours. The mixture was cooled, and partitioned between EtOAc and water. The organic phase was washed with brine, dried (MgSO4), filtered, and concentrated. Column chromatography (2-5% acetone/hexanes) followed by a second chromatography (2-20% EtOAc/hexanes) provided (Z)-N-(1-(4-(4-Isopropylphenyl)phenyl)-1-(3-thienyl)prop-1-en-3-yl)sarcosine, tbutyl ester F(i) (18.65 g, 81%) as a yellow oil. 1H NMR (300 MHz, CDCl3) 1.29 (d, 6H), 1.44 (s, 9H), 2.39 (s, 3H), 2.95 (hept, 1H), 3.16 (s, 2H), 3.30 (d, 2H), 6.26 (t, 1H), 6.93 (d, 1H), 7.18 (d, 1H), 7.26-7.35 (m, 5H), 7.50-7.54 (m, 4H).

Workup

  1. temperatureThe vigorously stirred mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe mixture was cooled
  4. custompartitioned between EtOAc and water
  5. washThe organic phase was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f6c4dedf6b8749218b54323a093b3bd4
Source dataset
uspto-grants-2003_12
Patent number
US06667336B2

Reaction notes

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