Benzyl Bromide → HCID 15434602, compound

HRID 1584575Notes

Reaction equation

HRID 1584575 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[C:14]1[CH2:18][CH2:17][CH2:16][C:15]=1[C:19]([O:21][CH3:22])=[O:20])=[CH:11][CH:10]=[C:9]([C:23]([OH:25])=[O:24])[CH:8]=2)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C)C=O>[CH2:28]([N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[C:9]([C:23]([OH:25])=[O:24])[CH:8]=2)[C:13]([C:14]2[CH2:18][CH2:17][CH2:16][C:15]=2[C:19]([O:21][CH3:22])=[O:20])=[C:5]1[CH2:1][CH2:2][CH2:3][CH3:4])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 15321707HCID 15321707, compound

Product 1

HCID 15434602HCID 15434602, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-butyl-3-(2-methoxycarbonyl-cyclopent-1-enyl)-1H-indole-6-carboxylic acid on Wang resin (100 mg; compound 7-1, prepared according to the procedure outlined in Example 7) in dimethylformamide (1.5 mL) was added sodium hydride (60% in mineral oil; 20 mg) and the mixture was stirred at room temperature for 30 min. Benzyl bromide (0.1 mL) was added and the mixture was stirred for 3 h. The mixture was filtered, washed with water (1×1.5 mL), tetrahydrofuran (2×1.5 mL), dichloromethane (2×1.5 mL), and dried. The product was cleaved from the resin by treatment with 1:1 trifluoroacetic acid/dichloromethane for 1 h; 1H NMR (DMSO-d6) δ 0.76 (t, 3 H), 1.20 (m, 2 H), 1.98 (m, 2 H), 2.00 (m, 2 H), 2.68 (t, 2 H), 2.82 (m, 4 H), 3.43 (s, 3 H), 5.56 (s, 2 H), 6.96 (d, 2 H), 7.30 (m, 4 H), 7.60 (d, 1 H), 7.90 (s, 1 H).

Workup

  1. stirringthe mixture was stirred for 3 h
  2. filtrationThe mixture was filtered
  3. washwashed with water (1×1.5 mL), tetrahydrofuran (2×1.5 mL), dichloromethane (2×1.5 mL)
  4. customdried
  5. waitThe product was cleaved from the resin by treatment with 1:1 trifluoroacetic acid/dichloromethane for 1 h

Sources & evidence

ORD record
ord-2224394a67424094b345dbf3c4d3083b
Source dataset
uspto-grants-1999_08
Patent number
US05932743

Reaction notes

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