Methyl 3-indoleglyoxylate → HCID 11502893, compound

HRID 2262659Notes

Reaction equation

HRID 2262659 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([N+:18]([O-:20])=[O:19])=[C:12]([CH2:14][C:15]([NH2:17])=[O:16])[CH:13]=2)[CH2:4][CH2:3]1.C[O:22][C:23](=O)[C:24]([C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[NH:28][CH:27]=1)=O.CC([O-])(C)C.[K+]>C1COCC1>[NH:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:26]([C:24]2[C:23](=[O:22])[NH:17][C:15](=[O:16])[C:14]=2[C:12]2[CH:13]=[C:8]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)[CH:9]=[CH:10][C:11]=2[N+:18]([O-:20])=[O:19])=[CH:27]1

Participants

5

Reactant 3

HCID 588944Methyl 3-indoleglyoxylateHCID 23665647Potassium tert-butoxideHCID 68686109HCID 68686109, compound

Product 1

HCID 11502893HCID 11502893, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-[5-(4-methyl-piperazin-1-yl)-2-nitro-phenyl]-acetamide (278 mg, 1.00 mmol) and (1H-indol-3-yl)-oxo-acetic acid methyl ester (366 mg, 1.80 mmol) in dry THF (8.0 mL) is added a solution of 1.0 M t-BuOK in THF (4.0 mL, 4.0 mmol) at 0° C. under argon. After stirring for 30 min at 0° C. and 1 h at RT, TLC indicates the complete consumption of the acetamide. The purple reaction mixture is partitioned between EtOAc (50 mL) and brine (50 mL), the layers are separated, and the aqueous layer is extracted with EtOAc (50 mL). The combined organic layers are dried over Na2SO4 and concentrated at reduced pressure. The crude product is purified by FCC (EtOAc/AcOH/H2O 7:1:1) to afford the title compound as its water soluble acetate salt. Orange solid. 1H NMR (DMSO-de, 400 MHz): δ 1.84 (s, 6H, CH3COO−), 1.97-2.15 (m, 4H), 2.03 (s, 3H), 2.95-3.21° (m, 4H), 6.51 (d, J=7.8 Hz, 1H), 6.54 (d, J=2.7 Hz, 1H), 6.73 (t, J=7.8 Hz, 1H), 7.01-7.07 (m, 2H), 7.41 (d, J=8.1 Hz, 1H), 8.00 (s, 1H), 8.13 (d, J=9.4 Hz, 1H), 10.8-11.4 (br, 1H), 11.95 (bs, 1H). ES+-MS: 431 [M+H]+.

Workup

  1. customthe complete consumption of the acetamide
  2. customThe purple reaction mixture is partitioned between EtOAc (50 mL) and brine (50 mL)
  3. customthe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (50 mL)
  5. dry with materialThe combined organic layers are dried over Na2SO4
  6. concentrationconcentrated at reduced pressure
  7. customThe crude product is purified by FCC (EtOAc/AcOH/H2O 7:1:1)

Sources & evidence

ORD record
ord-6f44af16a08842dca026e322364512a1
Source dataset
uspto-grants-2010_12
Patent number
US07851475B2

Reaction notes

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