Benzyl Bromide → HCID 11145063, compound

HRID 1584577Notes

Reaction equation

HRID 1584577 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[C:14]1[C:23]3[C:18](=[C:19]([O:24][CH3:25])[CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][CH:15]=1)=[CH:11][CH:10]=[C:9]([C:26]([OH:28])=[O:27])[CH:8]=2)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C)C=O>[CH2:31]([N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[C:9]([C:26]([OH:28])=[O:27])[CH:8]=2)[C:13]([C:14]2[C:23]3[C:18](=[C:19]([O:24][CH3:25])[CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][CH:15]=2)=[C:5]1[CH2:1][CH2:2][CH2:3][CH3:4])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 15434604HCID 15434604, compound

Product 1

HCID 11145063HCID 11145063, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-butyl-3-(5-methoxy-3,4-dihydro-naphthalen-1-yl)-1H-indole-6-carboxylic acid on Wang resin (100 mg; prepared according to the procedure outlined in Example 9) 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 0.67 (t, J=7.0 Hz, 3 H), 1.16 (t, J=6.7 Hz, 2 H), 1.34 (t, J=6.7 Hz, 2 H), 2.42 (m, 2 H), 2.55 (m, 2 H), 2.80 (m, 2 H), 3.82 (s, 3 H), 5.59 (s, 2 H), 6.12 (t, 1 H), 6.32 (d, J=7.3 Hz, 1 H), 6.88 (d, J=8.3 Hz, 1 H), 7.00 (m, 3 H), 7.15 (d, J=8.3 Hz, 1 H), 7.30 (m, 3 H), 7.55 (d, J=8.2 Hz, 1 H), 7.94 (s, 1 H).

Workup

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

Sources & evidence

ORD record
ord-ce561abdb5b44efc94c9ca7dbed82901
Source dataset
uspto-grants-1999_08
Patent number
US05932743

Reaction notes

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