Ethyl bromoacetate → HCID 67614058, compound

HRID 1584578Notes

Reaction equation

HRID 1584578 reaction equation
[CH3:1][O:2][C:3]1[CH:36]=[CH:35][C:6]([C:7]([N:9]([CH2:11][C:12]2[NH:13][C:14]3[C:19]([C:20]=2[C:21]2[C:31]#[C:30][C:24]4[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:23]=4[CH:22]=2)=[CH:18][CH:17]=[C:16]([C:32]([OH:34])=[O:33])[CH:15]=3)[CH3:10])=[O:8])=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42]>CN(C)C=O>[CH2:44]([O:43][C:41]([CH2:40][N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[C:16]([C:32]([OH:34])=[O:33])[CH:15]=2)[C:20]([C:21]2[C:31]#[C:30][C:24]3[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:23]=3[CH:22]=2)=[C:12]1[CH2:11][N:9]([C:7](=[O:8])[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:36][CH:35]=1)[CH3:10])=[O:42])[CH3:45]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 67613781HCID 67613781, compound

Product 1

HCID 67614058HCID 67614058, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-{[(4-methoxy-benzoyl)-methyl-amino]-methyl}-3-(benzocyclohept-1-enyl)-1H-indole-6-carboxylic acid on Wang resin (100 mg; prepared according to the procedure outlined in Example 10) 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. Ethyl bromoacetate (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 1.15 (t, 3 H), 2.10 (m, 2 H), 2.20 (m, 2 H), 2.70 (s, 3 H), 2.80 (m, 2 H), 3.80 (s, 3 H), 4.05 (q, 2 H), 4.80 (s, 2 H), 5.20 (br s, 2 H), 6.35 (t, 1 H), 6.80 (d, 1 H), 6.97 (d, 2 H), 7.08 (m, 2 H), 7.20 (m, 1 H), 7.38 (d, 2 H), 7.55 (d, 1 H), 7.80 (d, 1 H), 7.95 (s, 1 H), 11.40 (br 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-0f31111c9a2340349e9f083bb82227a9
Source dataset
uspto-grants-1999_08
Patent number
US05932743

Reaction notes

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