Butyric anhydride → HCID 11214749, compound

HRID 347368Notes

Reaction equation

HRID 347368 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[C:11]([O:32][CH3:33])=[CH:12][C:13]([O:30][CH3:31])=[C:14](/[CH:16]=[CH:17]/[C:18]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[O:19])[CH:15]=1.CCN(CC)CC.[CH2:41]1[CH2:45][O:44][CH2:43][CH2:42]1.C(OC(=O)CCC)(=O)CCC>CN(C1C=CN=CC=1)C.O>[C:43]([NH:29][S:26]([C:23]1[CH:22]=[CH:21][C:20]([C:18](/[CH:17]=[CH:16]/[C:14]2[CH:15]=[C:10]([C:2]3[NH:1][C:9]4[C:4]([CH:3]=3)=[CH:5][CH:6]=[CH:7][CH:8]=4)[C:11]([O:32][CH3:33])=[CH:12][C:13]=2[O:30][CH3:31])=[O:19])=[CH:25][CH:24]=1)(=[O:28])=[O:27])(=[O:44])[CH2:42][CH2:41][CH3:45]

Participants

7

Reactant 4

HCID 7798Butyric anhydrideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 210416274-{3E-[5-(1H-indol-2-yl)-2,4-dimethoxyphenyl]acryloyl}benzenesulfonamide

Product 1

HCID 11214749HCID 11214749, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

To a solution of 4-{3E-[5-(1H-indol-2-yl)-2,4-dimethoxyphenyl]acryloyl}benzenesulfonamide (Ex-35E, 0.92 g, 2 mmol), DMAP(0.024 g, 0.2 mmol) and Et3N (0.2 g, 2.1 mmol) in 100 ml o THF was added butyric anhydride (0.64 g, 4 mmol). The reaction mixture was stirred at room temperature overnight. The clear solution was then poured into 150 ml of H2O and extracted with CH2Cl2. The combined organic phase was washed with water, dried over MgSO4, and concentrated to dryness. Recrystallization from EtOAc/hexenes gave 0.80 g (75%) of the title compound as a red solid, mp 155–165° C. 1H-NMR (300 MHz, Acetone-d6) δ 10.55 (br, 1H), 8.35 (s, 1H), 8.27 (d, J=8 Hz, 2H), 8.13–8.20 (m, 3H), 7.89 (d, J=16 Hz, 1H), 7.52 (d, J=7 Hz, 1H), 7.39 (d, J=8 Hz, 1H), 7.02–7.07(m, 1H), 6.95–7.00 (m, 2H), 6.90 (s, 1H), 4.10 (s, 3H), 4.04 (s, 3H), 2.29 (t, J=8 Hz, 2H), 1.48–1.56 (m, 2H), 0.81(t, J=8 Hz, 3H).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined organic phase was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to dryness
  5. customRecrystallization from EtOAc/hexenes

Sources & evidence

ORD record
ord-902b056a3c8f40dc98887291f970ae74
Source dataset
uspto-grants-2007_02
Patent number
US07173129B2

Reaction notes

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