Methyl Acrylate → HCID 15292760, compound

HRID 2210604Notes

Reaction equation

HRID 2210604 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]2[N:13]3[CH:14]=[CH:15][C:16]([C:17]([C:19]4[C:27]5[C:22](=[CH:23][C:24]([C:28]6[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=6)=[CH:25][CH:26]=5)[NH:21][CH:20]=4)=[O:18])=[C:12]3[CH2:11][S:10]2)[CH:4]=1.[C:35]([O:39][CH3:40])(=[O:38])[CH:36]=[CH2:37]>CN(C=O)C.[Cl-].[Na+].O>[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]2[N:13]3[CH:14]=[CH:15][C:16]([C:17]([C:19]4[C:27]5[C:22](=[CH:23][C:24]([C:28]6[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=6)=[CH:25][CH:26]=5)[N:21]([CH2:37][CH2:36][C:35]([O:39][CH3:40])=[O:38])[CH:20]=4)=[O:18])=[C:12]3[CH2:11][S:10]2)[CH:4]=1

Participants

6

Reactant 3

HCID 7294Methyl AcrylateHCID 24758Sodium hydrideHCID 10717912HCID 10717912, compound

Product 1

HCID 15292760HCID 15292760, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium hydride (95%, 37.4 mg, 1.48 mmol) was added to a solution of 3-(pyridin-3-yl)-7-[6-(4-fluorophenyl)indol-3-ylcarbonyl]-1H,3H-pyrrolo[1,2-c]thiazole (0.50 g, 1.14 mmol), prepared according to the method of Example 28, in DMF (30 mL). The reaction mixture was stirred for 30 min. at ambient temperature, and then methyl acrylate (0.40 mL, 4.56 mmol) was added. The reaction mixture was poured into brine and extracted three times with ethyl acetate. The combined organic layers where dried over MgSO4, filtered, and concentrated in vacuo. 3-(Pyridin-3-yl)-7-[1-(2-carbomethoxyethyl)-6-(4-fluorophenyl)indol-3-ylcarbonyl]-1H,3H-pyrrolo[1,2-c]thiazole (190 mg, 32%) was obtained by flash chromatography on silica gel (5 g, 40%, then 60%, then 80% ethyl acetate, hexanes). 1H NMR (CDCl3, 300 MHz) δ2.93 (t, 2 H, J=6, 8 Hz), 3.68 (s, 3H), 4.53 (dd, 3H, J=6, 11 Hz), 4.7 (dd, 1H, J=2, 15 Hz), 6.38 (d, 1H, J=3 Hz), 6.43 (s, 1H), 6.78 (d, 1H, J=3 Hz), 7.15 (t, 2H, J=9, 10 Hz), 7.35 (dd, 1H, J=5, 8 Hz), 7.5 (dd, 2H, J=3, 10 Hz), 7.6-7.1 (m, 3H), 7.95 (s, 1H), 8.45 (dd, 1H, J=1, 9 Hz), 8.6-8.68 (m, 2H). MS (DCI/MH3) m/e 526 (M+H)+.

Workup

  1. customprepared
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic layers where dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c4064482e8214f9694f30613502e00e4
Source dataset
uspto-grants-1995_10
Patent number
US05459152

Reaction notes

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