Water → HCID 59129243, compound

HRID 1404027Notes

Reaction equation

HRID 1404027 reaction equation
[Br:1]N1C(=O)CCC1=O.[O:9]1[C:13]2[CH:14]=[CH:15][C:16]([C:18]3([C:21]([NH:23][C:24]4[CH:25]=[C:26]5[C:30](=[CH:31][CH:32]=4)[NH:29][CH:28]=[CH:27]5)=[O:22])[CH2:20][CH2:19]3)=[CH:17][C:12]=2[O:11][CH2:10]1.O>CN(C)C=O>[O:9]1[C:13]2[CH:14]=[CH:15][C:16]([C:18]3([C:21]([NH:23][C:24]4[CH:25]=[C:26]5[C:30](=[CH:31][CH:32]=4)[NH:29][CH:28]=[C:27]5[Br:1])=[O:22])[CH2:20][CH2:19]3)=[CH:17][C:12]=2[O:11][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 24762493HCID 24762493, compound

Product 1

HCID 59129243HCID 59129243, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Freshly recrystallized N-bromosuccinimide (0.278 g, 1.56 mmol) was added portionwise to a solution of 1-(benzo[d][1,3]dioxol-5-yl)-N-(1H-indol-5-yl)cyclopropanecarboxamide (0.500 g, 1.56 mmol) in N,N-dimethylformamide (2 mL) over 2 minutes. The reaction mixture was protected from light and was stirred bar for 5 minutes. The resulting green solution was poured into 40 mL of water. The grey precipitate which formed was filtered and washed with water to yield 1-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-1H-indol-5-yl)cyclopropanecarboxamide (0.564 g, 91%). ESI-MS m/z calc. 398.0, found 399.3 (M+1)+. Retention time of 3.38 minutes. 1H NMR (400 MHz, DMSO-d6) 11.37 (s, 1H), 8.71 (s, 1H), 7.67 (d, J=1.8 Hz, 1H), 7.50 (d, J=2.6 Hz, 1H), 7.29 (d, J=8.8 Hz, 1H), 7.22 (dd, J=2.0, 8.8 Hz, 1H), 7.02 (d, J=1.6 Hz, 1H), 6.96-6.88 (m, 2H), 6.03 (s, 2H), 1.43-1.40 (m, 2H), 1.09-1.04 (m, 2H).

Workup

  1. customThe grey precipitate which formed
  2. filtrationwas filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-b7507ac8a4ee44a594a5bd5ccbaf243d
Source dataset
uspto-grants-2014_12
Patent number
US08912199B2

Reaction notes

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