Triethylamine → (E)-3-(4-{1-[2-(2-tert-butyl-6-nitro-1H-indol-3-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester

HRID 549384Notes

Reaction equation

HRID 549384 reaction equation
[C:1]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[CH2:14][CH:15]=O)=[CH:11][CH:10]=[C:9]([N+:17]([O-:19])=[O:18])[CH:8]=2)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:21][O:22][C:23](=[O:37])/[CH:24]=[CH:25]/[C:26]1[CH:31]=[CH:30][C:29]([CH:32]2[CH2:36][CH2:35][CH2:34][NH:33]2)=[CH:28][CH:27]=1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:21][O:22][C:23](=[O:37])/[CH:24]=[CH:25]/[C:26]1[CH:31]=[CH:30][C:29]([CH:32]2[CH2:36][CH2:35][CH2:34][N:33]2[CH2:15][CH2:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([N+:17]([O-:19])=[O:18])=[CH:10][CH:11]=3)[NH:6][C:5]=2[C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 57899287(2-tert-butyl-6-nitro-1H-indol-3-yl)-acetaldehydeHCID 67158154(E)-3-(4-pyrrolidin-2-yl-phenyl)-acrylic acid methyl ester hydrochloride

Product 1

HCID 57899242(E)-3-(4-{1-[2-(2-tert-butyl-6-nitro-1H-indol-3-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl esterYield 57.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-tert-butyl-6-nitro-1H-indol-3-yl)-acetaldehyde (0.74 g, 2.8 mmol) in tetrahydrofuran (20 mL) was added (E)-3-(4-pyrrolidin-2-yl-phenyl)-acrylic acid methyl ester hydrochloride (0.91 g, 3.4 mmol) and triethylamine (871 μL, 6.26 mmol). The resulting mixture was stirred at room temperature for 1 h and sodium triacetoxyborohydride (0.88 g, 4.0 mmol) was added. The mixture was stirred at room temperature for 16 h, diluted with ethyl acetate, and washed with a saturated sodium bicarbonate and a saturated aqueous solution of sodium chloride. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel column chromatography to give the title compound (0.77 g, 57%). LCMS (m/z): 476.2539 (M+1).

Workup

  1. stirringThe mixture was stirred at room temperature for 16 h
  2. washwashed with a saturated sodium bicarbonate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-5250863c25f1498994429c2fe513eb14
Source dataset
uspto-grants-2011_05
Patent number
US07943652B2

Reaction notes

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