Toluene → HCID 22603442, compound

HRID 2307914Notes

Reaction equation

HRID 2307914 reaction equation
C(OC(OC(C)(C)C)N(C)C)(C)(C)C.[Br:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[C:17]=1[C:34]([OH:36])=[O:35].[C:37]1(C)[CH:42]=CC=[CH:39][CH:38]=1>>[Br:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([Cl:33])[CH:27]=2)[C:17]=1[C:34]([O:36][CH:37]([CH2:38][CH3:39])[CH3:42])=[O:35]

Participants

4

Reactant 3

HCID 1140TolueneHCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 22603404HCID 22603404, compound

Product 1

HCID 22603442HCID 22603442, compound

Procedure

N,N-dimethylformamide di-t-butyl acetal (19.90 ml) was added dropwise to a suspension of 3-bromo-N-(3,4-dichlorobenzyl)indole-2-carboxylic acid (8.31 g) in toluene (150 ml), under an atmosphere of argon, and stirred at ambient temperature for 2 hours. The reaction was cooled, filtered, and washed with brine (100 ml), saturated NaHCO3 (aq.) (100 ml), and brine (100 ml), dried (MgSO4) and concentrated in vacuo to afford the product as a clear oil that crystallised upon standing (7.65 g, 81%); NMR d (CD3SOCD3) 1.49 (s, 9H), 5.76 (s, 2H), 6.86 (m, 1H), 7.24 (t, 1H), 7.35-7.68 (m, 5H); M/z (+) 456 (MH−), 400.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. washwashed with brine (100 ml), saturated NaHCO3 (aq.) (100 ml), and brine (100 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-37ca3d4e9c1e46d78d57d8268026cb45
Source dataset
uspto-grants-2004_12
Patent number
US06833387B1

Reaction notes

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