Iodoethane → HCID 22676833, compound

HRID 1006263Notes

Reaction equation

HRID 1006263 reaction equation
I[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH:10]1([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([OH:30])[CH:28]=4)[N:23]([CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=4)[C:22]=3[C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:17][CH:16]=2)[CH2:12][CH2:11]1>CN(C=O)C.C(OCC)(=O)C>[CH:10]1([CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH2:2][CH3:3])[CH:28]=4)[N:23]([CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=4)[C:22]=3[C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:19][CH:20]=2)[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 22676725HCID 22676725, compound

Product 1

HCID 22676833HCID 22676833, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Iodoethane (468 mg, 3.0 mmol) and powdered potassium carbonate (138 mg, 1.0 mmol) was added to a solution of ethyl 3-[4-(cyclopropylmethoxy)phenyl]-5-hydroxy-1-(3-methoxybenzyl)-1H-indole-2-carboxylate (Example 66, 120 mg, 0.25 mmol) in DMF (5 mL). The mixture was heated (50° C.) for 16 h and then cooled. The resulting mixture was diluted with ethyl acetate (50 mL), washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative TLC using 4:1 ethyl acetate/hexane as the eluant, to afford 52 mg (42%) of the desired product. The product had: 1H NMR (300 MHz, acetone-D6) δ 7.42 (d, 1 H), 7.37 (d, 2 H), 7.19 (t, 1 H), 6.92-7.01 (m 4 H), 6.74-6.77 (m, 1 H), 6.64-6.68 (m, 2 H), 5.80 (s, 2 H), 4.13 (q, 2 H), 3.88-3.98 (m, 4 H), 3.69 (s, 3 H), 1.34-1.45 (m, 4 H), 1.04 (t, 3 H), 0.56-0.66 (m, 2 H), 0.34-0.44 (m, 2 H).

Workup

  1. temperaturecooled
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-1880f056ead04af8bd11aff5d22ec8d9
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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