Hydrochloric Acid → HCID 86743691, compound

HRID 330168Notes

Reaction equation

HRID 330168 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22](/[CH:25]=[C:26](/[C:28](=[O:33])[NH:29][CH2:30][CH2:31][CH3:32])\[CH3:27])[CH:23]=2)[NH:18][CH:17]=1)[C:8]([O:10][CH3:11])=[O:9].[CH2:34](Br)[CH:35]=[CH2:36].Cl>CN(C)C=O.O>[CH2:36]([N:18]1[C:19]2[C:24](=[CH:23][C:22](/[CH:25]=[C:26](/[C:28](=[O:33])[NH:29][CH2:30][CH2:31][CH3:32])\[CH3:27])=[CH:21][CH:20]=2)[C:16]([CH2:15][C:14]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=2[O:4][CH3:3])=[CH:17]1)[CH:35]=[CH2:34]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 67834674HCID 67834674, compound

Product 1

HCID 86743691HCID 86743691, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.048 g of a 60% dispersion in oil) was added to a stirred solution of methyl E-3-methoxy-4-[5-[2-(propylcarbamoyl)-1-propenyl]indol-3-ylmethyl]benzoate (0.5 g) in N,N-dimethylformamide (5 ml), under an atmosphere of nitrogen. After 0.5 hr, allyl bromide (0.14 g) was added and stirring continued for 3 hr. The solution was acidified with 1M hydrochloric acid (10 ml), diluted with water (20 ml), extracted with ethyl acetate (twice), and the organic phase was washed with water (4 times), brine, and dried (MgSO4). The solvent was evaporated to give an oil which was purified by flash chromatography, eluting with 2:1:1 hexane:methylene chloride:ethyl acetate, to give methyl E-4[1-allyl-5-[2-(propylcarbamoyl)-1-propenyl]indol-3-ylmethyl)-3-methoxybenzoate (0.36 g, 66%) as a white foam; partial NMR (250 MHz, DMSO-d6) 0.87(t, 3H, CH2CH2CH3), 1.47(m, 2 H, CH2CH2CH3), 1.99(s, 3H, CCH3), 3.11(m, 2H, CH2CH2CH3), 3.83(s, 3H, OCH3), 3.90(s, 3H, OCH3), 4.06(s, 2H, ArCH2Ar'), 4.77(br d, J=5.3 Hz, 2H, NCH2CH:C), 5.00-5.16(m, 2H, olefinic H), 6.0(m, 1H, olefinic H), 7.94(br t, 1H, NHCO).

Workup

  1. waitcontinued for 3 hr
  2. extractionextracted with ethyl acetate (twice), and the organic phase
  3. washwas washed with water (4 times), brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated
  6. customto give an oil which
  7. customwas purified by flash chromatography
  8. washeluting with 2:1:1 hexane

Sources & evidence

ORD record
ord-ab717b65ad85417a83b2bbb60a31d93c
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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