Acetic Acid → 1-[3-(1,3-Dioxolan-2-yl)benzyl]-7-cyanomethoxyindole

HRID 1198551Notes

Reaction equation

HRID 1198551 reaction equation
[H-].[Na+].[C:3]([CH2:5][O:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[CH:12]2)#[N:4].[O:16]1[CH2:20][CH2:19][O:18][CH:17]1[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Br.C(O)(=O)C>O1CCCC1.ClCCl>[O:16]1[CH2:20][CH2:19][O:18][CH:17]1[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][N:14]1[C:15]2[C:11](=[CH:10][CH:9]=[CH:8][C:7]=2[O:6][CH2:5][C:3]#[N:4])[CH:12]=[CH:13]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 150540207-(Cyanomethoxy)indoleHCID 191025633-(1,3-Dioxolan-2-yl)benzyl bromide

Product 1

HCID 191026031-[3-(1,3-Dioxolan-2-yl)benzyl]-7-cyanomethoxyindole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

60% Sodium hydride dispersion in mineral oil (90 mg, 2.25 mmol) was added to a stirred, cooled solution of 7-cyanomethoxyindole (Example 1a) (0.32 g., 1.86 mmol) in tetrahydrofuran (8 ml). The dark mixture was stirred for 15 minutes at room temperature then cooled again whilst a solution of 3-(1,3-dioxolan-2-yl)benzyl bromide (0.50 g., 2.06 mmol) in tetrahydrofuran (2 ml) was added. The mixture was stirred at room temperature for 20 hours then treated with glacial acetic acid (130 μl), diluted with dichloromethane, washed with water, dried and evaporated. The residue was chromatographed on silica in ethyl acetate-hexane (1:3).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature for 20 hours
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica in ethyl acetate-hexane (1:3)

Sources & evidence

ORD record
ord-482a656edc4e4126845732fd2c629cc9
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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